메뉴 건너뛰기




Volumn 2, Issue 11, 2003, Pages 1187-1199

Acid-controlled photoreactions of aryl alkanoates: Competition of transesterification, decarboxylation, Fries-rearrangement and/or transposition

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRIMETHYLPHENYL (MESITYL) CYCLOHEXANECARBOXYLATE; 2,6 DIMETHYLPHENYL (XYLENYL), PHENYL, 4 METHOXYPHENYL (4 ANISYL) ALKANOATE; 4 METHOXYNAPHTHYL ALKANOATE; ACETONITRILE; ALKANE DERIVATIVE; ALKYLBENZENE; ALKYLMESITYLENE; ARYL ALKANOATE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXADIENONE; CYCLOHEXYLMESITYLENE; ESTER DERIVATIVE; MESITYL ESTER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

EID: 2442649648     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b305898k     Document Type: Article
Times cited : (16)

References (147)
  • 3
    • 27944441732 scopus 로고    scopus 로고
    • note
    • A study of photodecarboxylation of simple aliphatic carboxylic acids was carried out in the gas phase and gave more complicated results due to several competing reactions; see also ref. 1.
  • 5
    • 50749134032 scopus 로고
    • Photodecarboxylation: Mechanism and synthetic utility
    • (b) D. Budac and P. J. Wan, Photodecarboxylation: mechanism and synthetic utility, J. Photochem. Photobiol., A, 1992, 67, 135-166.
    • (1992) J. Photochem. Photobiol., A , vol.67 , pp. 135-166
    • Budac, D.1    Wan, P.J.2
  • 6
    • 9444222661 scopus 로고
    • Photochemistry of substituted 1-naphthylmethyl esters of phenylacetic and 3-phenylpropanoic acid: Radical pairs, ion pairs, and Marcus electron transfer
    • (a) D. P. DeCosta and J. A. Pincock, Photochemistry of substituted 1-naphthylmethyl esters of phenylacetic and 3-phenylpropanoic acid: radical pairs, ion pairs, and Marcus electron transfer, J. Am. Chem. Soc., 1993, 115, 2180-2190;
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 2180-2190
    • DeCosta, D.P.1    Pincock, J.A.2
  • 7
    • 0000047779 scopus 로고
    • Homolytic versus heterolytic cleavage for the photochemistry of 1-naphthylmethyl derivatives
    • (b) B. Arnold, L. Donald, A. Jurgens and J. A. Pincock, Homolytic versus heterolytic cleavage for the photochemistry of 1-naphthylmethyl derivatives, Can. J. Chen., 1985, 63, 3140-3146;
    • (1985) Can. J. Chen. , vol.63 , pp. 3140-3146
    • Arnold, B.1    Donald, L.2    Jurgens, A.3    Pincock, J.A.4
  • 8
    • 0006480136 scopus 로고
    • Photodecarboxylation. A labeling study. Mechanistic studies in photochemistry. 15
    • and references cited therein
    • R. S. Givens, B. Matuszewski, N. Levi and D. Leung, Photodecarboxylation. A labeling study. Mechanistic studies in photochemistry. 15, J. Am. Chem. Soc., 1977, 99, 1896-1903 and references cited therein.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 1896-1903
    • Givens, R.S.1    Matuszewski, B.2    Levi, N.3    Leung, D.4
  • 9
    • 0001238134 scopus 로고    scopus 로고
    • Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters
    • (a) A. Banerjee and D. E. Falvey, Protecting groups that can be removed through photochemical electron transfer: Mechanistic and product studies on photosensitized release of carboxylates from phenacyl esters, J. Org. Chem., 1997, 62, 6245-6251;
    • (1997) J. Org. Chem. , vol.62 , pp. 6245-6251
    • Banerjee, A.1    Falvey, D.E.2
  • 10
    • 0000858509 scopus 로고
    • Fragmentation of substituted acetophenones and halobenzophenone ketyls. Calibration of a mechanistic probe
    • (b) D. D. Tanner, J. J. Chen, L. Chen and C. Leulo, Fragmentation of substituted acetophenones and halobenzophenone ketyls. Calibration of a mechanistic probe, J. Am. Chem. Soc., 1991, 113, 8074-8081.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8074-8081
    • Tanner, D.D.1    Chen, J.J.2    Chen, L.3    Leulo, C.4
  • 11
    • 0030755239 scopus 로고    scopus 로고
    • New photoactivated protecting groups. 7. p-Hydroxyphenacyl: A phototrigger for excitatory amino acids and peptides
    • (a) R. S. Givens, A. Jung, C.-H. Park, J. Weber and W. Bartlett, New photoactivated protecting groups. 7. p-Hydroxyphenacyl: A phototrigger for excitatory amino acids and peptides, J. Am. Chem. Soc., 1997, 119, 8369-8370;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 8369-8370
    • Givens, R.S.1    Jung, A.2    Park, C.-H.3    Weber, J.4    Bartlett, W.5
  • 12
    • 37049090871 scopus 로고
    • P-Methoxyphcnacyl esters as photodeblockable protecting groups for phosphates
    • (b) W. W. Epstein and M. Garrossian, p-Methoxyphcnacyl esters as photodeblockable protecting groups for phosphates, J. Chem. Soc., Chem. Commun., 1987, 532-533;
    • (1987) J. Chem. Soc., Chem. Commun. , pp. 532-533
    • Epstein, W.W.1    Garrossian, M.2
  • 13
    • 0001315370 scopus 로고
    • Phenacyl photosensitive blocking groups
    • J. C. Sheehan and K. Umezawa, Phenacyl photosensitive blocking groups, J. Org. Chem., 1973, 38, 3771-3774;
    • (1973) J. Org. Chem. , vol.38 , pp. 3771-3774
    • Sheehan, J.C.1    Umezawa, K.2
  • 14
    • 0001383523 scopus 로고
    • Photolysis of methoxy-substituted benzoin esters. Photosensitive protectinc group forcarboxylic acids
    • J. C. Sheehan, R. M. Wilson and A. W. Oxford, Photolysis of methoxy-substituted benzoin esters. Photosensitive protectinc group forcarboxylic acids, J Am. Chem. Soc., 1971, 93, 7222-7228;
    • (1971) J Am. Chem. Soc. , vol.93 , pp. 7222-7228
    • Sheehan, J.C.1    Wilson, R.M.2    Oxford, A.W.3
  • 15
    • 0001416056 scopus 로고
    • The phenacyl protecting group for acids and phenols
    • J. B. Hendrickson and C. Kandall, The phenacyl protecting group for acids and phenols, Tetrahedron Lett., 1970, 11, 343-344;
    • (1970) Tetrahedron Lett. , vol.11 , pp. 343-344
    • Hendrickson, J.B.1    Kandall, C.2
  • 16
    • 33947483984 scopus 로고
    • Photolysis of desyl compounds. A new photolytic cyclization
    • (f) J. C. Sheehan and R. M. Wilson, Photolysis of desyl compounds. A new photolytic cyclization, J. Am. Chem. Soc., 1964, 86, 5277-5281;
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5277-5281
    • Sheehan, J.C.1    Wilson, R.M.2
  • 17
    • 0442283671 scopus 로고
    • A photo-induced rearrangement involving aryl participation
    • (g) J. C. Anderson and C. B. Reese, A photo-induced rearrangement involving aryl participation, Tetrahedron Lett., 1962, 3, 1-4.
    • (1962) Tetrahedron Lett. , vol.3 , pp. 1-4
    • Anderson, J.C.1    Reese, C.B.2
  • 19
    • 0000619884 scopus 로고    scopus 로고
    • Photo-Fries rearraneement
    • For reveiws on photo-Fries reactions, see: (a) E. Rusu, E. Comanita and M. Onciu, Photo-Fries rearraneement, Rouman. Chem. Quart. Rev., 2000, 7, 241-250;
    • (2000) Rouman. Chem. Quart. Rev. , vol.7 , pp. 241-250
    • Rusu, E.1    Comanita, E.2    Onciu, M.3
  • 20
    • 84952129306 scopus 로고
    • Uses of the Fries rearrangement for the preparation of hydroxyaryl ketones. A review
    • (b) R. Martin, Uses of the Fries rearrangement for the preparation of hydroxyaryl ketones. A review., Org. Prep. Proc. Int., 1992, 24, 369-435;
    • (1992) Org. Prep. Proc. Int. , vol.24 , pp. 369-435
    • Martin, R.1
  • 21
    • 0006994946 scopus 로고
    • Photochemical rearrangements and fragmentations of benzene derivatives and anellated arenes
    • G. Kaupp, Photochemical rearrangements and fragmentations of benzene derivatives and anellated arenes, Angew. Chem., Int. Ed. Engl., 1980, 19, 243-275;
    • (1980) Angew. Chem., Int. Ed. Engl. , vol.19 , pp. 243-275
    • Kaupp, G.1
  • 22
    • 0001080532 scopus 로고
    • Photo-Fries rearrangement and related photochemical [1,j]-shifts (j = 3, 5, 7) of carbonyl and sulfonyl groups
    • D. Bellus, Photo-Fries rearrangement and related photochemical [1,j]-shifts (j = 3, 5, 7) of carbonyl and sulfonyl groups, Adv. Photochem., 1971, 8, 109-159.
    • (1971) Adv. Photochem. , vol.8 , pp. 109-159
    • Bellus, D.1
  • 23
    • 0000265685 scopus 로고
    • Photolytic deprotection and activation of functional groups
    • the tosyl group has been successively used as a photoliable protecting group. See, for example
    • For a general review on photoprotecting groups: (a) V. N. R. Pillai, Photolytic deprotection and activation of functional groups, Org. Photochem., 1987, 9, 225-323; the tosyl group has been successively used as a photoliable protecting group. See, for example;
    • (1987) Org. Photochem. , vol.9 , pp. 225-323
    • Pillai, V.N.R.1
  • 24
    • 0039040160 scopus 로고
    • Hydrolysis of tosyl esters initiated by an electron transfer from photoexcited electron-rich aromatic compounds
    • (b) A. Nishida, T. Hamada and O. Yonemitsu, Hydrolysis of tosyl esters initiated by an electron transfer from photoexcited electron-rich aromatic compounds, J. Org. Chem., 1988, 53, 3386-3387;
    • (1988) J. Org. Chem. , vol.53 , pp. 3386-3387
    • Nishida, A.1    Hamada, T.2    Yonemitsu, O.3
  • 25
    • 0040224106 scopus 로고
    • Inside-outside stereoisomerism. II. Synthesis of the carbocyclic ring system of the ingenane diterpenes via the intramolecular dioxolenone photocycloaddition
    • J. Masnovi, D. J. Koholic, R. J. Berki and R. W. Binkley, Inside-outside stereoisomerism. II. Synthesis of the carbocyclic ring system of the ingenane diterpenes via the intramolecular dioxolenone photocycloaddition, J. Am. Chem. Soc., 1987, 109, 2851-2853;
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2851-2853
    • Masnovi, J.1    Koholic, D.J.2    Berki, R.J.3    Binkley, R.W.4
  • 26
    • 0011554672 scopus 로고    scopus 로고
    • Photochemical removal of the tosyl group from the 5′N position of 5′-aminopyrimidine nucleosides: Synthetic applications
    • Tris(trimethylsilyl)silyl and other silyl ethers
    • W. Urjasz and L. Celewicz, Photochemical removal of the tosyl group from the 5′N position of 5′-aminopyrimidine nucleosides: synthetic applications, J. Phys. Org. Chem., 1998, 11, 618-621 Tris(trimethylsilyl)silyl and other silyl ethers:;
    • (1998) J. Phys. Org. Chem. , vol.11 , pp. 618-621
    • Urjasz, W.1    Celewicz, L.2
  • 27
    • 0030854225 scopus 로고    scopus 로고
    • The sisyl (tris(trimethylsilyl)silyl) group: A fluoride resistant, photolabile alcohol protecting group
    • (e) M. A. Brook, C. Gottardo, S. Balduzzi and M. Mohamed, The sisyl (tris(trimethylsilyl)silyl) group: A fluoride resistant, photolabile alcohol protecting group, Tetrahedron Lett., 1997, 38, 6997-7000;
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6997-7000
    • Brook, M.A.1    Gottardo, C.2    Balduzzi, S.3    Mohamed, M.4
  • 28
    • 0000999179 scopus 로고
    • Photochemically-removable silyl protecting groups
    • (f) M. C. Pirrung and Y. R. Lee, Photochemically-removable silyl protecting groups, J. Org. Chem., 1993, 58, 6961-6963;
    • (1993) J. Org. Chem. , vol.58 , pp. 6961-6963
    • Pirrung, M.C.1    Lee, Y.R.2
  • 30
    • 0030854225 scopus 로고    scopus 로고
    • The sisyl (tris(trimethylsilyl)silyl) group: A fluoride resistant, photolabile alcohol protecting group
    • (h) M. A. Brook, C. Gottardo, S. Balduzzi and M. Mohamed, The sisyl (tris(trimethylsilyl)silyl) group: a fluoride resistant, photolabile alcohol protecting group, Tetrahedron Lett., 1997, 38, 6997-7000.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6997-7000
    • Brook, M.A.1    Gottardo, C.2    Balduzzi, S.3    Mohamed, M.4
  • 31
    • 0001323365 scopus 로고    scopus 로고
    • Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate
    • For a preliminary communication, see: T. Mori, T. Wada and Y. Inoue, Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate, Org. Lett., 2000, 2, 3401-3404;
    • (2000) Org. Lett. , vol.2 , pp. 3401-3404
    • Mori, T.1    Wada, T.2    Inoue, Y.3
  • 32
    • 0037023422 scopus 로고    scopus 로고
    • Novel [2 + 2] photocycloaddition-induced rearrangement of bichromophoric naphthalene-tethered resorcinol ethers
    • see, also: (a) N. Hoffmann, J.-P. Pete, Y. Inoue and T. Mori, Novel [2 + 2] photocycloaddition-induced rearrangement of bichromophoric naphthalene-tethered resorcinol ethers, J. Org. Chem., 2002, 67, 2315-2322;
    • (2002) J. Org. Chem. , vol.67 , pp. 2315-2322
    • Hoffmann, N.1    Pete, J.-P.2    Inoue, Y.3    Mori, T.4
  • 33
    • 0034760858 scopus 로고    scopus 로고
    • Photoinduced electron-transfer oxidation of olefins with molecular oxygen sensitized by tetrasubstituted dimethoxybenzenes: A non-singlet-oxygen mechanism
    • (b) T. Mori, M. Takamoto, T. Wada and Y. Inoue, Photoinduced electron-transfer oxidation of olefins with molecular oxygen sensitized by tetrasubstituted dimethoxybenzenes: a non-singlet-oxygen mechanism, Helv. Chim. Acta, 2001, 84, 2693-2707;
    • (2001) Helv. Chim. Acta , vol.84 , pp. 2693-2707
    • Mori, T.1    Takamoto, M.2    Wada, T.3    Inoue, Y.4
  • 34
    • 0035952977 scopus 로고    scopus 로고
    • Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: A non-singlet-oxygen mechanism
    • T. Mori, M. Takamoto, Y. Tale, J. Shinkuma, T. Wada and Y. Inoue, Photoinduced electron transfer oxidation of α-methylstyrene with molecular oxygen sensitized by dimethoxybenzenes: a non-singlet-oxygen mechanism, Tetrahedron Lett., 2001, 42, 2505-25087
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2505-25087
    • Mori, T.1    Takamoto, M.2    Tale, Y.3    Shinkuma, J.4    Wada, T.5    Inoue, Y.6
  • 35
    • 0000406490 scopus 로고    scopus 로고
    • Proton-assisted switching of reaction pathways of stilbene analogues broueht by direct irradiation
    • Recently, the importance of acid catalysis has been recognized in various photoreactions. For other examples, see: (a) J.-H. Ho, T.-I. Ho and R. S. H. Liu, Proton-assisted switching of reaction pathways of stilbene analogues broueht by direct irradiation, Org. Lett., 2001, 3, 409-411;
    • (2001) Org. Lett. , vol.3 , pp. 409-411
    • Ho, J.-H.1    Ho, T.-I.2    Liu, R.S.H.3
  • 36
    • 0033828710 scopus 로고    scopus 로고
    • Novel Acid-catalyzed hydrolysis of an intermediate from a photorearrangement of stilbenes
    • (b) T.-I. Ho, J.-H. Ho and J. Y. Wu, Novel Acid-catalyzed hydrolysis of an intermediate from a photorearrangement of stilbenes, J. Am. Chem. Soc., 2000, 122, 8575-8576;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8575-8576
    • Ho, T.-I.1    Ho, J.-H.2    Wu, J.Y.3
  • 37
    • 0034703203 scopus 로고    scopus 로고
    • The Phototransposition in acetonitrile and the photoaddition of 2,2,2-trifluoroethanol to the six isomers of dimethylbenzonitrile
    • N. Howell, J. A. Pincock and R. Stefanova, The Phototransposition in acetonitrile and the photoaddition of 2,2,2-trifluoroethanol to the six isomers of dimethylbenzonitrile, J. Org. Chem., 2000, 65, 6173-6178;
    • (2000) J. Org. Chem. , vol.65 , pp. 6173-6178
    • Howell, N.1    Pincock, J.A.2    Stefanova, R.3
  • 39
    • 0033106157 scopus 로고    scopus 로고
    • Stereo- and regioselectivity of intramolecular 1,2-arene-alkene photocycloaddition in 2-alkenyl-4-chromanones
    • (e) G. P. Kalena, P. Pradhan and A. Banerji, Stereo- and regioselectivity of intramolecular 1,2-arene-alkene photocycloaddition in 2-alkenyl-4- chromanones, Tetrahedron, 1999, 55, 3209-3218;
    • (1999) Tetrahedron , vol.55 , pp. 3209-3218
    • Kalena, G.P.1    Pradhan, P.2    Banerji, A.3
  • 40
    • 0032500075 scopus 로고    scopus 로고
    • Acid catalyzed intramolecular [2+2] photocycloaddition of 3,5-dihydroxybenzoic acid derivatives
    • (f) N. Hoffman and J.-P. Pete, Acid catalyzed intramolecular [2+2] photocycloaddition of 3,5-dihydroxybenzoic acid derivatives, Tetrahedron Lett., 1998, 39, 5027-5030;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5027-5030
    • Hoffman, N.1    Pete, J.-P.2
  • 41
    • 0001686098 scopus 로고    scopus 로고
    • Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil in frozen benzene: Formation of photocycloadducts and their isomerization through photo-Diels-Alder reaction
    • (g) K. Ohkura, Y. Noguchi and K. Seki, Acid-catalyzed photoreaction of 6-chloro-1,3-dimethyluracil in frozen benzene: formation of photocycloadducts and their isomerization through photo-Diels-Alder reaction, Heterocycles, 1998, 47, 429-437;
    • (1998) Heterocycles , vol.47 , pp. 429-437
    • Ohkura, K.1    Noguchi, Y.2    Seki, K.3
  • 42
    • 0000127808 scopus 로고    scopus 로고
    • Intramolecular photochemical reactions of bichromophoric 3-(alkenyloxy)phenols and 1-(alkenyloxy)-3-(alkyloxy)benzene derivatives. Acid-catalyzed transformations of the primary cycloadducts
    • (h) N. Hoffman and J.-P. Pete, Intramolecular photochemical reactions of bichromophoric 3-(alkenyloxy)phenols and 1-(alkenyloxy)-3-(alkyloxy)benzene derivatives. Acid-catalyzed transformations of the primary cycloadducts, J. Org. Chem., 1997, 62, 6952-6960;
    • (1997) J. Org. Chem. , vol.62 , pp. 6952-6960
    • Hoffman, N.1    Pete, J.-P.2
  • 44
    • 0001658310 scopus 로고    scopus 로고
    • Photochemical and acid-catalyzed rearrangements of 4-carbomethoxy-4- methyl-3-(trimethylsilyl)-2,5-cyclohexadien-1-one
    • (j) A. G. Schultz and E. G. Antoulinakis, Photochemical and acid-catalyzed rearrangements of 4-carbomethoxy-4-methyl-3-(trimethylsilyl)-2,5- cyclohexadien-1-one, J. Org. Chem., 1996, 61, 4555-4559;
    • (1996) J. Org. Chem. , vol.61 , pp. 4555-4559
    • Schultz, A.G.1    Antoulinakis, E.G.2
  • 45
    • 0027156938 scopus 로고
    • Synthesis of cyclooctapyrimidine-2,4-diones by photocycloaddition of 6-chloro-1,3-dimethyluracil to benzenes in the presence of trifluoroacetic acid
    • (k) K. Ohkura, N. Kanazashi and K. Seki, Synthesis of cyclooctapyrimidine-2,4-diones by photocycloaddition of 6-chloro-1,3- dimethyluracil to benzenes in the presence of trifluoroacetic acid, Chem. Pharm. Bull., 1993, 41, 239-243;
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 239-243
    • Ohkura, K.1    Kanazashi, N.2    Seki, K.3
  • 46
    • 0026688708 scopus 로고
    • A novel intramolecular 1,2-arene-alkene photocycloaddition
    • P. Kalena, P. Pradhan and A. Banerji, A novel intramolecular 1,2-arene-alkene photocycloaddition, Tetrahedron Lett., 1992, 33, 7775-7778;
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7775-7778
    • Kalena, P.1    Pradhan, P.2    Banerji, A.3
  • 47
    • 0000803135 scopus 로고
    • The photocycloaddition of naphthoates with acetylacetone; dramatic acid promotions of product quantum yields
    • Y. L. Chow and X. Liu, The photocycloaddition of naphthoates with acetylacetone; dramatic acid promotions of product quantum yields, Can. J. Chem., 1991, 69, 1261-1272;
    • (1991) Can. J. Chem. , vol.69 , pp. 1261-1272
    • Chow, Y.L.1    Liu, X.2
  • 48
    • 0002003320 scopus 로고
    • Photocyclization of stilbenes and related molecules
    • (n) F. B. Mallory and C. W. Mallory, Photocyclization of stilbenes and related molecules, Org. React. (New York), 1984, 30, 1-456.
    • (1984) Org. React. (New York) , vol.30 , pp. 1-456
    • Mallory, F.B.1    Mallory, C.W.2
  • 49
    • 0001681416 scopus 로고
    • Spectroscopic and kinetic characteristics of aroyloxyl radicals. 1. The 4-methoxybenzoyloxyl radical
    • In the study of 4-methoxybenzoyloxyl radical produced by laser flash photolysis, it was reported that at least three or more species are responsible for 320 nm absorption in carbon tetrachloride. In acetonitrile, the 4-methoxybenzoyloxyl radical seems to be the most probable species responsible for this absorption. See, for in detail: (a) J. Chateauneuf, J. Lusztyk and K. U. Ingold, Spectroscopic and kinetic characteristics of aroyloxyl radicals. 1. The 4-methoxybenzoyloxyl radical, J. Am. Chem. Soc., 1988, 110, 2877-2885;
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2877-2885
    • Chateauneuf, J.1    Lusztyk, J.2    Ingold, K.U.3
  • 50
    • 2742524683 scopus 로고
    • Spectroscopic and kinetic characteristics of aroyloxyl radicals. 2. Benzoyloxyl and ring-substituted aroyloxyl radicals
    • (b) J. Chateauneuf, J. Lusztyk and K. U. Ingold, Spectroscopic and kinetic characteristics of aroyloxyl radicals. 2. Benzoyloxyl and ring-substituted aroyloxyl radicals, J. Am. Chem. Soc., 1988, 110, 2886-2893.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2886-2893
    • Chateauneuf, J.1    Lusztyk, J.2    Ingold, K.U.3
  • 52
    • 0000158437 scopus 로고
    • Photophysical properties of methylated phenols in nonpolar solvents
    • (a) G. Grabner, G. Köhler, G. Marconi, S. Monti and E. Venuti, Photophysical properties of methylated phenols in nonpolar solvents, J. Phys. Chem., 1990, 94, 3609-3613;
    • (1990) J. Phys. Chem. , vol.94 , pp. 3609-3613
    • Grabner, G.1    Köhler, G.2    Marconi, G.3    Monti, S.4    Venuti, E.5
  • 53
    • 0000563497 scopus 로고
    • Mechanistic study of the termination reactions of 2,4,6-trialkylphenoxy radicals carboxylic acids
    • (b) S. A. Weiner and L. R. Mahoney, Mechanistic study of the termination reactions of 2,4,6-trialkylphenoxy radicals carboxylic acids, J. Am. Chem. Soc., 1972, 94, 5029-5033; see also;
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 5029-5033
    • Weiner, S.A.1    Mahoney, L.R.2
  • 54
    • 33947294687 scopus 로고
    • Kinetic and thermochemical study of the reaction of 2,4,6-tri-tert- butylphenoxy radical with substituted phenols
    • L. R. Mahoney and M. A. DaRooge, Kinetic and thermochemical study of the reaction of 2,4,6-tri-tert-butylphenoxy radical with substituted phenols, J. Am. Chem. Soc., 1970, 92, 890-899;
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 890-899
    • Mahoney, L.R.1    Darooge, M.A.2
  • 55
    • 0000867823 scopus 로고
    • Quinone dehydrogcnation. I. The oxidation of monohydric phenols
    • H.-D. Becker, Quinone dehydrogcnation. I. The oxidation of monohydric phenols, J. Org. Chem., 1965, 30, 982-989.
    • (1965) J. Org. Chem. , vol.30 , pp. 982-989
    • Becker, H.-D.1
  • 56
    • 0000129279 scopus 로고
    • Free radical combination reactions involving phenoxyl radicals
    • However, there was no spectroscopic (UV-vis) evidence for the existence of such a mesityl radical, absorbing at 395 (in hexane) or 396 nm (in water). See: M. Jonsson, J. Lind, T. Reitberger, T. E. Eiksen and O. Merényi, Free radical combination reactions involving phenoxyl radicals, J. Phys. Chem., 1993, 97, 8229-8233.
    • (1993) J. Phys. Chem. , vol.97 , pp. 8229-8233
    • Jonsson, M.1    Lind, J.2    Reitberger, T.3    Eiksen, T.E.4    Merényi, O.5
  • 57
    • 27944440988 scopus 로고    scopus 로고
    • note
    • -1, respectively.
  • 58
    • 0032770704 scopus 로고    scopus 로고
    • Scandium triflate in organic synthesis
    • 3] has recently been used extensively in various types of catalytic and stoichiometric reactions, especially in the presence of water or similar nucleophiles. See, for instance: (a) S. Kobayashi, Scandium triflate in organic synthesis, Eur. J. Org. Chem., 1999, 15-27;
    • (1999) Eur. J. Org. Chem. , pp. 15-27
    • Kobayashi, S.1
  • 59
    • 37049080896 scopus 로고
    • A novel Mannich-type reaction in aqueous media. Lanthanide triflate-catalyzed condensation of aldehydes, amines and vinyl ethers for the synthesis of β-amino ketones
    • (b) S. Kobayashi and H. Ishitani, A novel Mannich-type reaction in aqueous media. Lanthanide triflate-catalyzed condensation of aldehydes, amines and vinyl ethers for the synthesis of β-amino ketones, J. Chem. Soc., Chem. Commun., 1995, 1379;
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 1379
    • Kobayashi, S.1    Ishitani, H.2
  • 60
    • 85064667331 scopus 로고
    • Rare earth metal trifluoromethanesulfonates as water-tolerant Lewis acid catalysts in organic synthesis
    • S. Kobayashi, Rare earth metal trifluoromethanesulfonates as water-tolerant Lewis acid catalysts in organic synthesis, Synlett, 1994, 689-701;
    • (1994) Synlett , pp. 689-701
    • Kobayashi, S.1
  • 61
    • 0002615814 scopus 로고
    • 3 catalyzed hydroxymethylation reaction of silyl enol ethers with commercial formaldehyde solution
    • 3 catalyzed hydroxymethylation reaction of silyl enol ethers with commercial formaldehyde solution, Chem. Lett., 1991, 2187-2190.
    • (1991) Chem. Lett. , pp. 2187-2190
    • Kobayashi, S.1
  • 62
    • 27944474778 scopus 로고    scopus 로고
    • note
    • Note that none or trace of phenolic product was obtained in the photolysis of 1c in Table 1. However, under similar conditions (Table 2), mesitol 10 was a minor product observed in the same (but different batch) solvent systems employed. It was reported previously that such less-reproducible changes of the product distribution in photo-Fries rearrangement do indeed happen, although the reason was not clear. In our cases, the results were repoducible as far as the same batch of solvent was used.
  • 63
    • 0000934768 scopus 로고    scopus 로고
    • Investigation of the photo-Fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. Comparison with the acid-catalyzed reactions
    • See also: C. Cui, X. Wang and R. G. Weiss, Investigation of the photo-Fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. Comparison with the acid-catalyzed reactions, J. Org. Chem., 1996, 61, 1962-1974.
    • (1996) J. Org. Chem. , vol.61 , pp. 1962-1974
    • Cui, C.1    Wang, X.2    Weiss, R.G.3
  • 64
    • 0141624470 scopus 로고    scopus 로고
    • Two-photon processes in the photo-Claisen and photo-Fries rearrangements. Direct observation of dienic ketenes generated by photolysis of transient cyclohexa-2,4-dienones
    • M. C. Jiménez, M. A. Miranda, J. C. Scaiano and R. Tormos, Two-photon processes in the photo-Claisen and photo-Fries rearrangements. Direct observation of dienic ketenes generated by photolysis of transient cyclohexa-2,4-dienones, Chem. Commun., 1997, 1487-1488.
    • (1997) Chem. Commun. , pp. 1487-1488
    • Jiménez, M.C.1    Miranda, M.A.2    Scaiano, J.C.3    Tormos, R.4
  • 65
    • 84982334291 scopus 로고
    • Nuclear magnetic resonance spectrometric detection of intramolecular mobility. II. Cis-trans, isomerism of ortho-substituted acetanilides
    • (a) H. Kessler and A. Rieker, Nuclear magnetic resonance spectrometric detection of intramolecular mobility. II. Cis-trans, isomerism of ortho-substituted acetanilides, Justus Liebigs Ann. Chem., 1967, 708, 57-68;
    • (1967) Justus Liebigs Ann. Chem. , vol.708 , pp. 57-68
    • Kessler, H.1    Rieker, A.2
  • 66
    • 3242776464 scopus 로고
    • Detection of intramolecular mobility by nuclear magnetic resonance spectroscopy. I. Cis-trans, isomers of ring-substituted acetanilides
    • (b) H. Kessler and A. Rieker, Detection of intramolecular mobility by nuclear magnetic resonance spectroscopy. I. Cis-trans, isomers of ring-substituted acetanilides, Z. Naturforsch., Teil B, 1967, 22, 456-457.
    • (1967) Z. Naturforsch., Teil B , vol.22 , pp. 456-457
    • Kessler, H.1    Rieker, A.2
  • 67
    • 0041180851 scopus 로고
    • Conformations of the esters. IV. Conformations of carbamates
    • (a) M. Oki and H. Nakanishi, Conformations of the esters. IV. Conformations of carbamates, Bull. Chem. Soc. Jpn., 1971, 44, 3148-3151;
    • (1971) Bull. Chem. Soc. Jpn. , vol.44 , pp. 3148-3151
    • Oki, M.1    Nakanishi, H.2
  • 68
    • 0141624733 scopus 로고
    • Determination of conformations of esters with the use of lanthanide shift reagents
    • (b) K. Sakamoto and M. Oki, Determination of conformations of esters with the use of lanthanide shift reagents, Bull. Chem. Soc. Jpn., 1974, 47, 2623-2624.
    • (1974) Bull. Chem. Soc. Jpn. , vol.47 , pp. 2623-2624
    • Sakamoto, K.1    Oki, M.2
  • 69
    • 0001609834 scopus 로고
    • Nuclear magnetic resonance study of exchanging systems. X. Rotational barriers to trans-cis isomerization in esters
    • H. Nakanishi, H. Fujita and O. Yamamoto, Nuclear magnetic resonance study of exchanging systems. X. Rotational barriers to trans-cis isomerization in esters, Bull. Chem. Soc. Jpn., 1978, 51, 214-218.
    • (1978) Bull. Chem. Soc. Jpn. , vol.51 , pp. 214-218
    • Nakanishi, H.1    Fujita, H.2    Yamamoto, O.3
  • 70
    • 0037065289 scopus 로고    scopus 로고
    • Observations of different triplet conformations in time-resolved infrared spectra of alkyl phenylglyoxylates
    • A. G. Merzlikine, S. V. Voskresensky, E. O. Danilov, M. A. J. Rodgers and D. C. Neckers, Observations of different triplet conformations in time-resolved infrared spectra of alkyl phenylglyoxylates, J. Am. Chem. Soc., 2002, 124, 14532-14533.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14532-14533
    • Merzlikine, A.G.1    Voskresensky, S.V.2    Danilov, E.O.3    Rodgers, M.A.J.4    Neckers, D.C.5
  • 71
    • 0037184768 scopus 로고    scopus 로고
    • Phototransposition reactions of methyl-substituted benzotrifluorides: Proof of the role of trifluoromethyl-substituted carbon
    • (a) D. DeCosta and J. Pincock, Phototransposition reactions of methyl-substituted benzotrifluorides: Proof of the role of trifluoromethyl- substituted carbon, J. Org. Chem., 2002, 67, 9484-9487;
    • (2002) J. Org. Chem. , vol.67 , pp. 9484-9487
    • DeCosta, D.1    Pincock, J.2
  • 72
    • 27944472690 scopus 로고    scopus 로고
    • note
    • (b) ref. 8b;
  • 73
  • 74
    • 0001736819 scopus 로고
    • Photochemical isomerization of di-t-butylbenzenes
    • A. W. Burgstahler and P.-L. Chien, Photochemical isomerization of di-t-butylbenzenes, J. Am. Chem. Soc., 1964, 86, 2940-2941;
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2940-2941
    • Burgstahler, A.W.1    Chien, P.-L.2
  • 75
    • 33947486510 scopus 로고
    • Photoisomerization of dialkylbenzenes
    • (e) K. E. Wilzbach and L. Kaplan, Photoisomerization of dialkylbenzenes, J. Am. Chem. Soc., 1964, 86, 2307-2308;
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2307-2308
    • Wilzbach, K.E.1    Kaplan, L.2
  • 77
    • 11144330936 scopus 로고
    • Evidence for a ladenburg benzene intermediate in the photo-isomerization of 1,2,4,5-tetrabutylbenzene to 1,2,3,5-tetrabutylbenzene
    • (g) E. M. Arnett and J. M. Bollinger, Evidence for a ladenburg benzene intermediate in the photo-isomerization of 1,2,4,5-tetrabutylbenzene to 1,2,3,5-tetrabutylbenzene, Tetrahedron Lett., 1964, 5, 3803-3808.
    • (1964) Tetrahedron Lett. , vol.5 , pp. 3803-3808
    • Arnett, E.M.1    Bollinger, J.M.2
  • 78
    • 0042301272 scopus 로고
    • Photorearrangcments of 2,4-disubstituted phenyl esters
    • J. S. Bradshaw, E. L. Loveridge and L. White, Photorearrangcments of 2,4-disubstituted phenyl esters, J. Org. Chem., 1968, 33, 4127-4132.
    • (1968) J. Org. Chem. , vol.33 , pp. 4127-4132
    • Bradshaw, J.S.1    Loveridge, E.L.2    White, L.3
  • 79
    • 0004707012 scopus 로고
    • [2.2]Paracyclophane by photoextrusion of carbon dioxide from a cyclic diester
    • (a) M. L. Kaplan and E. A. Truesdale, [2.2]Paracyclophane by photoextrusion of carbon dioxide from a cyclic diester, Tetrahedron Lett., 1976, 17, 3665-3666;
    • (1976) Tetrahedron Lett. , vol.17 , pp. 3665-3666
    • Kaplan, M.L.1    Truesdale, E.A.2
  • 80
    • 3242761673 scopus 로고
    • [2.2.2.2] Orthoparacyclophane
    • (b) E. L. Truesdale, [2.2.2.2] Orthoparacyclophane, Tetrahedron Lett., 1978, 19, 3777-3780;
    • (1978) Tetrahedron Lett. , vol.19 , pp. 3777-3780
    • Truesdale, E.L.1
  • 81
    • 0004726566 scopus 로고
    • Substituent effect during the synthesis of substituted [2.2] paracyclophane by photoextrusion of carbon dioxide from a cyclic diester
    • M. Hilbert and G. Solladie, Substituent effect during the synthesis of substituted [2.2] paracyclophane by photoextrusion of carbon dioxide from a cyclic diester, J. Org. Chem., 1980, 45, 4496-3398.
    • (1980) J. Org. Chem. , vol.45 , pp. 4496-13398
    • Hilbert, M.1    Solladie, G.2
  • 82
    • 84878809664 scopus 로고
    • Quantum yields in the photochemically induced radical chemistry of acyl derivatives of thiohydroxamic acids
    • (a) D. H. L. Barton and J. C. Jaszbcrenyi, Quantum yields in the photochemically induced radical chemistry of acyl derivatives of thiohydroxamic acids, J. Am. Chem. Soc., 1991, 113, 6937-6942;
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6937-6942
    • Barton, D.H.L.1    Jaszbcrenyi, J.C.2
  • 83
    • 4243854308 scopus 로고
    • Radical chemistry associated with the thiocarbonyl group
    • (b) D. Crich and L. Quintero, Radical chemistry associated with the thiocarbonyl group, Chem. Rev., 1989, 89, 1413-1432;
    • (1989) Chem. Rev. , vol.89 , pp. 1413-1432
    • Crich, D.1    Quintero, L.2
  • 84
    • 0001069743 scopus 로고
    • Photochemistry of hydroxamic acids and derivatives
    • E. Lipczynska-Kochany, Photochemistry of hydroxamic acids and derivatives, Chem. Rev., 1991, 91, 477-491;
    • (1991) Chem. Rev. , vol.91 , pp. 477-491
    • Lipczynska-Kochany, E.1
  • 85
    • 0000407138 scopus 로고
    • Control of stereochemistry in free radical reactions with oxazolidine auxiliaries
    • N. A. Porter, J. D. Bruhnke, W.-X. Wu, I. J. Rosenstein and R. A. Breyer, Control of stereochemistry in free radical reactions with oxazolidine auxiliaries, J. Am. Chem. Soc., 1991, 113, 7788-7790;
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7788-7790
    • Porter, N.A.1    Bruhnke, J.D.2    Wu, W.-X.3    Rosenstein, I.J.4    Breyer, R.A.5
  • 86
    • 0002801332 scopus 로고
    • O-Acyl thiohydroxamates: New and versatile sources of alkyl radicals for use in organic synthesis
    • (e) D. Crich, O-Acyl thiohydroxamates: new and versatile sources of alkyl radicals for use in organic synthesis, Aldrichim. Acta, 1987, 20, 35-42.
    • (1987) Aldrichim. Acta , vol.20 , pp. 35-42
    • Crich, D.1
  • 87
    • 27944476389 scopus 로고    scopus 로고
    • note
    • (a) Ref. 3(b);
  • 88
    • 0000032042 scopus 로고
    • Rates of decarboxylation of acyloxy radicals formed in the photocleavage of substituted 1-naphthylmethyl alkanoates
    • (b) J. W. Hilborn and J. A. Pincock, Rates of decarboxylation of acyloxy radicals formed in the photocleavage of substituted 1-naphthylmethyl alkanoates, J. Am. Chem. Soc., 1991, 113, 2683-2686;
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2683-2686
    • Hilborn, J.W.1    Pincock, J.A.2
  • 89
    • 33845373620 scopus 로고
    • Picosecond time scale dynamics of perester photodecomposition: Evidence for an acyloxy radical intermediate in the photolysis of tert-butyl 9-methylfluorene-9-percarboxylate
    • D. E. Falvey and G. B. Schuster, Picosecond time scale dynamics of perester photodecomposition: evidence for an acyloxy radical intermediate in the photolysis of tert-butyl 9-methylfluorene-9-percarboxylate, J. Am. Chem. Soc., 1986, 108, 7419-8420;
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7419-8420
    • Falvey, D.E.1    Schuster, G.B.2
  • 90
    • 0010295178 scopus 로고
    • Chemically induced dynamic nuclear polarization. XI. Thermal decomposition of acetyl peroxide
    • R. Kaptein, J. Brokken-Zijp and F. J. J. de Kanter, Chemically induced dynamic nuclear polarization. XI. Thermal decomposition of acetyl peroxide, J. Am. Chem. Soc., 1972, 94, 6280-6287;
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6280-6287
    • Kaptein, R.1    Brokken-Zijp, J.2    De Kanter, F.J.J.3
  • 91
    • 0001133694 scopus 로고
    • Peroxide decomposition and cage effect
    • (e) W. Braun, L. Rajibenbach and F. R. Eirich, Peroxide decomposition and cage effect, J. Phys. Chem., 1962, 66, 1591-1595.
    • (1962) J. Phys. Chem. , vol.66 , pp. 1591-1595
    • Braun, W.1    Rajibenbach, L.2    Eirich, F.R.3
  • 92
    • 15844415139 scopus 로고    scopus 로고
    • Direct observation of carbon-carbon bond cleavage in ultrafast decarboxylations
    • Recently, charge transfer acitivation of alkoxyl radicals such as benzilates and fluorenecarboxylates in the presence of methylviologen has been studied in detail using fs time-resolved spectroscopies to reveal the mechanism incorporating the initial photoinduced electron transfer followed by a fast decarboxylation within 1-2 ns. (a) T. M. Bockman, S. M. Hubig and J. K. Kochi, Direct observation of carbon-carbon bond cleavage in ultrafast decarboxylations, J. Am. Chem. Soc., 1996, 118, 4502-1503;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4502-11503
    • Bockman, T.M.1    Hubig, S.M.2    Kochi, J.K.3
  • 93
    • 0000834065 scopus 로고    scopus 로고
    • Direct observation of ultrafast decarboxylation of acyloxy radicals via photoinduced electron transfer in carboxylate ion pairs
    • (b) T. M. Bockman, S. M. Hubig and J. K. Kochi, Direct observation of ultrafast decarboxylation of acyloxy radicals via photoinduced electron transfer in carboxylate ion pairs, J. Org. Chem., 1997, 62, 2210-2221.
    • (1997) J. Org. Chem. , vol.62 , pp. 2210-2221
    • Bockman, T.M.1    Hubig, S.M.2    Kochi, J.K.3
  • 94
    • 0010605740 scopus 로고
    • Photo-induced decarboxylation of aliphatic acids and esters in solution. Dependence upon state of protonation of the carboxyl group
    • L. J. Mittal, J. P. Mittal and E. Hayon, Photo-induced decarboxylation of aliphatic acids and esters in solution. Dependence upon state of protonation of the carboxyl group, J. Phys. Chem., 1973, 77, 1482-1487.
    • (1973) J. Phys. Chem. , vol.77 , pp. 1482-1487
    • Mittal, L.J.1    Mittal, J.P.2    Hayon, E.3
  • 95
    • 0013856316 scopus 로고
    • Photodecarboxylation process; preparation of some hindered aryl ketones
    • R. A. Finnegan and D. Knutson, Photodecarboxylation process; preparation of some hindered aryl ketones, Chem. Ind. (London), 1965, 1837-1838.
    • (1965) Chem. Ind. (London) , pp. 1837-1838
    • Finnegan, R.A.1    Knutson, D.2
  • 96
    • 0005699485 scopus 로고
    • Stereochemistry of photodecarboxylation and photodecarbonylation reactions of aryl esters. The photolysis of (S)-(+)-3,5-di-t-butylphenyl 2-methylbutanoate
    • R. A. Finnegan and D. Knutson, Stereochemistry of photodecarboxylation and photodecarbonylation reactions of aryl esters. The photolysis of (S)-(+)-3,5-di-t-butylphenyl 2-methylbutanoate, J. Am. Chem. Soc., 1967, 89, 1970-1972.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1970-1972
    • Finnegan, R.A.1    Knutson, D.2
  • 97
    • 0141455987 scopus 로고    scopus 로고
    • Complete memory of chirality upon photodecarboxylation of mesityl alkanoate to mesitylalkane: Theoretical and experimental evidence for cheletropic decarboxylation via spiro-lactonic transition state
    • DOI: 10.1039/b305267b
    • T. Mori, H. Saito and Y. Inoue, Complete memory of chirality upon photodecarboxylation of mesityl alkanoate to mesitylalkane: Theoretical and experimental evidence for cheletropic decarboxylation via spiro-lactonic transition state, Chem. Commun., 2003, DOI: 10.1039/b305267b.
    • (2003) Chem. Commun.
    • Mori, T.1    Saito, H.2    Inoue, Y.3
  • 98
    • 0000944753 scopus 로고
    • Mechanistic studies of the photo-Fries reaction
    • (a) M. R. Sander, E. Hedaya and D. J. Trecker, Mechanistic studies of the photo-Fries reaction, J Am. Chem. Soc., 1968, 90, 7249-7254;
    • (1968) J Am. Chem. Soc. , vol.90 , pp. 7249-7254
    • Sander, M.R.1    Hedaya, E.2    Trecker, D.J.3
  • 99
    • 0013166927 scopus 로고
    • Mechanism of the photo-Fires reaction
    • (b) M. R. Sander and D. J. Trecker, Mechanism of the photo-Fires reaction, J. Am. Chem. Soc., 1967, 89, 5725-5726;
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 5725-5726
    • Sander, M.R.1    Trecker, D.J.2
  • 100
    • 55549116045 scopus 로고
    • The photochemical Fries reaction
    • J. C. Anderson and C. B. Reese, The photochemical Fries reaction, J. Chem. Soc., 1963, 1781-1784.
    • (1963) J. Chem. Soc. , pp. 1781-1784
    • Anderson, J.C.1    Reese, C.B.2
  • 101
    • 0001497430 scopus 로고
    • Photochemical studies-II: The photo-rearrangement of aryl esters
    • (a) R. A. Finnegan and J. J. Mattice, Photochemical studies-II: The photo-rearrangement of aryl esters, Tetrahedron, 1965, 21, 1015-1026;
    • (1965) Tetrahedron , vol.21 , pp. 1015-1026
    • Finnegan, R.A.1    Mattice, J.J.2
  • 102
    • 0037969033 scopus 로고
    • The photo-Fries reaction of aryl esters: Effect of solvent on production distribution
    • (b) D. A. Plank, The photo-Fries reaction of aryl esters: effect of solvent on production distribution, Tetrahedron Lett., 1968, 9, 5423-5426;
    • (1968) Tetrahedron Lett. , vol.9 , pp. 5423-5426
    • Plank, D.A.1
  • 103
    • 27944436171 scopus 로고
    • A study of selected photo Fries rearrangements
    • CAS No. 87:38600
    • E. L. Loveridge, A study of selected photo Fries rearrangements, Diss. Abstr. Int. B, 1977, 37, 5087 (CAS No. 87:38600).
    • (1977) Diss. Abstr. Int. B , vol.37 , pp. 5087
    • Loveridge, E.L.1
  • 104
    • 0000155122 scopus 로고
    • Rearrangement of aromatic esters by ultraviolet radiation
    • H. Kobsa, Rearrangement of aromatic esters by ultraviolet radiation, J. Org. Chem., 1962, 27, 2293-2298.
    • (1962) J. Org. Chem. , vol.27 , pp. 2293-2298
    • Kobsa, H.1
  • 105
    • 37049059156 scopus 로고
    • The photochemical decomposition of some aryl esters
    • W. M. Horspool and P. L. Parson, The photochemical decomposition of some aryl esters, J. Chem. Soc., 1965, 5162-5166.
    • (1965) J. Chem. Soc. , pp. 5162-5166
    • Horspool, W.M.1    Parson, P.L.2
  • 106
    • 0343805521 scopus 로고
    • Photo-Fries rearrangement of aromatic esters. Role of steric and electronic factors
    • G. M. Coppinger and E. R. Bell, Photo-Fries rearrangement of aromatic esters. Role of steric and electronic factors, J. Phys. Chem., 1966, 70, 3479-3489.
    • (1966) J. Phys. Chem. , vol.70 , pp. 3479-3489
    • Coppinger, G.M.1    Bell, E.R.2
  • 108
    • 0002821185 scopus 로고
    • Fluorescence quenching of methoxybenzyl alcohols by the hydronium ion in aqueous solution: Acid-catalyzed formation of methoxybenzyl cations from the singlet excited state
    • The pH dependence on photobehaviour has been studied extensively. See, for example: N. J. Turro and P. Wan, Fluorescence quenching of methoxybenzyl alcohols by the hydronium ion in aqueous solution: acid-catalyzed formation of methoxybenzyl cations from the singlet excited state, J. Photochem., 1985, 28, 93-102.
    • (1985) J. Photochem. , vol.28 , pp. 93-102
    • Turro, N.J.1    Wan, P.2
  • 109
    • 0003924674 scopus 로고
    • Mercel Dekker, Inc., New York, 2nd edn.
    • -1 at 25 °C in EtOH and MeCN, respectively. See: S. L. Murov, I. Carmichael and G. L. Hug, in Handbook of Photochemistry, Mercel Dekker, Inc., New York, 2nd edn., 1993, p. 210.
    • (1993) Handbook of Photochemistry , pp. 210
    • Murov, S.L.1    Carmichael, I.2    Hug, G.L.3
  • 112
    • 0003970635 scopus 로고
    • Cambridge University Press, London, for susceptibilities of aromatic esters toward electrophlic substitutions, see
    • K. Schofield, in Aromatic Nitration; Cambridge University Press, London, 1980;; for susceptibilities of aromatic esters toward electrophlic substitutions, see
    • (1980) Aromatic Nitration
    • Schofield, K.1
  • 113
    • 37049080491 scopus 로고
    • Ozone-mediated reaction of anilides and phenyl esters with nitrogen dioxide: Enhanced ortho-reactivity and mechanistic implications
    • H. Suzuki, A. Tatsumi, T. Ishibashi and T. Mori, Ozone-mediated reaction of anilides and phenyl esters with nitrogen dioxide: enhanced ortho-reactivity and mechanistic implications, J. Chem. Soc., Perkin Trans. 1, 1995, 339-343.
    • (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 339-343
    • Suzuki, H.1    Tatsumi, A.2    Ishibashi, T.3    Mori, T.4
  • 114
    • 27944449678 scopus 로고    scopus 로고
    • note
    • The significant decrease in reaction rate in the presence of oxygen may support this hypothesis, although the singlet excited state is also quenched by oxygen. Reaction of the ester-acid complex with oxygen may be another rationalization for the decreased rate of conversion.
  • 115
    • 0000884562 scopus 로고
    • Photosolvolyses and attendant photoreactions involving carbocations
    • For reviews on photosolvolysis, see: (a) S. J. Cristol and T. H. Bindel, Photosolvolyses and attendant photoreactions involving carbocations, Org. Photochem., 1983, 6, 327-415;
    • (1983) Org. Photochem. , vol.6 , pp. 327-415
    • Cristol, S.J.1    Bindel, T.H.2
  • 116
    • 27944491252 scopus 로고    scopus 로고
    • note
    • (b) ref. 1(b).
  • 117
    • 0011480120 scopus 로고
    • The photoinduced alcoholysis of 3,4-dihydrocoumarin and related compounds
    • (a) C. D. Gutsche and B. A. Oude-Alink, The photoinduced alcoholysis of 3,4-dihydrocoumarin and related compounds, J. Am. Chem. Soc., 1968, 90, 5855-5861;
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5855-5861
    • Gutsche, C.D.1    Oude-Alink, B.A.2
  • 118
    • 27944479010 scopus 로고    scopus 로고
    • note
    • (b) ref. 34(c).
  • 119
    • 0347784711 scopus 로고
    • Photochemical studies. VI. Photochemistry of nitrobenzoate esters and related nitroaromatic compounds. Some novel reduction and esterification reactions
    • R. A. Finnegan and D. Knutson, Photochemical studies. VI. Photochemistry of nitrobenzoate esters and related nitroaromatic compounds. Some novel reduction and esterification reactions, J. Am. Chem. Soc., 1968, 90, 1670-1671.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 1670-1671
    • Finnegan, R.A.1    Knutson, D.2
  • 120
    • 27944493964 scopus 로고    scopus 로고
    • note
    • However, the effect of acid was not simple. We will report this in detail in a separate paper in due course, using isolable analogous cyclohexadienones.
  • 121
    • 0000718262 scopus 로고
    • Proton-induced electron-transfer reaction from triplet methoxynaphthalenes to benzophenone via triplet exciplex
    • (a) M. Yamaji, T. Sekiguchi, M. Hoshino and H. Shizuka, Proton-induced electron-transfer reaction from triplet methoxynaphthalenes to benzophenone via triplet exciplex, J. Phys. Chem., 1992, 96, 9353-9359;
    • (1992) J. Phys. Chem. , vol.96 , pp. 9353-9359
    • Yamaji, M.1    Sekiguchi, T.2    Hoshino, M.3    Shizuka, H.4
  • 122
    • 1542587138 scopus 로고    scopus 로고
    • Charge-transfer absorption of olefins with nitrosonium. Structural relevance to the dimethylbutene complex with dinitrogen tetraoxide
    • (b) E. Bosch and J. K. Kochi, Charge-transfer absorption of olefins with nitrosonium. Structural relevance to the dimethylbutene complex with dinitrogen tetraoxide, Res. Chem. Intermed, 1996, 22, 209-224;
    • (1996) Res. Chem. Intermed , vol.22 , pp. 209-224
    • Bosch, E.1    Kochi, J.K.2
  • 123
    • 0029875368 scopus 로고    scopus 로고
    • Catalytic epoxidation of hindered olefins with dioxygen. Fast oxygen atom transfer to olefin cation radicals from nitrogen oxides
    • E. Bosch and J. K. Kochi, Catalytic epoxidation of hindered olefins with dioxygen. Fast oxygen atom transfer to olefin cation radicals from nitrogen oxides, J. Am. Chem. Soc., 1996, 118, 1319-1329;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1319-1329
    • Bosch, E.1    Kochi, J.K.2
  • 124
    • 0001438636 scopus 로고    scopus 로고
    • Generation and reactions of radical cations from the photolysis of aromatic compounds with tetranitromethane in 1,1,1,3,3,3-hexafluoropropan-2-ol
    • L. Eberson, O. Persson, F. Radner and M. P. Hartshorn, Generation and reactions of radical cations from the photolysis of aromatic compounds with tetranitromethane in 1,1,1,3,3,3-hexafluoropropan-2-ol, Res. Chem. Intermed., 1996, 22, 799-820;
    • (1996) Res. Chem. Intermed. , vol.22 , pp. 799-820
    • Eberson, L.1    Persson, O.2    Radner, F.3    Hartshorn, M.P.4
  • 125
    • 33749082093 scopus 로고
    • Detection and reactions of radical cations generated by photolysis of aromatic compounds with tetranitromethane in 1,2,2,3,3,3-hexafluoro-2-propanol at room temperature
    • (e) L. Eberson, M. P. Hartshorn and O. Persson, Detection and reactions of radical cations generated by photolysis of aromatic compounds with tetranitromethane in 1,2,2,3,3,3-hexafluoro-2-propanol at room temperature, Angew. Chem., Int. Ed. Engl., 1995, 34, 2268-2269;
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2268-2269
    • Eberson, L.1    Hartshorn, M.P.2    Persson, O.3
  • 126
    • 0001767309 scopus 로고
    • Direct nitrosation of aromatic hydrocarbons and ethers with the electrophilic nitrosonium cation
    • (f) E. Bosch and J. K. Kochi, Direct nitrosation of aromatic hydrocarbons and ethers with the electrophilic nitrosonium cation, J. Org. Chem., 1994, 59, 5573-5586;
    • (1994) J. Org. Chem. , vol.59 , pp. 5573-5586
    • Bosch, E.1    Kochi, J.K.2
  • 127
    • 33845185534 scopus 로고
    • Oxidative aromatic nitration with charge-transfer complexes of arenes and nitrosonium salts
    • (g) K. E. Kim and J. K. Kochi, Oxidative aromatic nitration with charge-transfer complexes of arenes and nitrosonium salts, J. Org. Chem., 1989, 54, 1692-1702;
    • (1989) J. Org. Chem. , vol.54 , pp. 1692-1702
    • Kim, K.E.1    Kochi, J.K.2
  • 128
    • 2142660464 scopus 로고
    • Thermal and photochemical nitration of aromatic hydrocarbons with nitrogen dioxide
    • (h) E. Bosch and J. K. Kochi, Thermal and photochemical nitration of aromatic hydrocarbons with nitrogen dioxide, J. Org. Chem., 1994, 59, 3314-3325.
    • (1994) J. Org. Chem. , vol.59 , pp. 3314-3325
    • Bosch, E.1    Kochi, J.K.2
  • 130
    • 0032494449 scopus 로고    scopus 로고
    • Mechanism of reaction of an arenediazonium ion in aqueous solutions of acetamide, N-methylacetamide, and N,N-dimethylacetamide. A potential method for chemically tagcing peptide bonds at acgregate interfaces
    • L. S. Romsted, J. Zhang and L. Zhuang, Mechanism of reaction of an arenediazonium ion in aqueous solutions of acetamide, N-methylacetamide, and N,N-dimethylacetamide. A potential method for chemically tagcing peptide bonds at acgregate interfaces, J. Am. Chem. Soc., 1998, 120, 10046-10054.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10046-10054
    • Romsted, L.S.1    Zhang, J.2    Zhuang, L.3
  • 132
    • 0028281283 scopus 로고
    • Friedel-Crafts cyclohexylation of arenes with 1,3- dicyclohexylcarbodiimide (DCC)
    • (a) J. N. Kim, K. H. Chung and E. K. Ryu, Friedel-Crafts cyclohexylation of arenes with 1,3-dicyclohexylcarbodiimide (DCC), Tetrahedron Lett., 1994, 35, 903-904;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 903-904
    • Kim, J.N.1    Chung, K.H.2    Ryu, E.K.3
  • 133
    • 0032917310 scopus 로고    scopus 로고
    • A new convenient Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates in the presence of scandium(III) trifluoromethanesulfonate or trifluoromethanesulfonic acid as the catalyst
    • (b) H. Kotsuki, T. Ohishi, M. Inoue and T. Kojima, A new convenient Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates in the presence of scandium(III) trifluoromethanesulfonate or trifluoromethanesulfonic acid as the catalyst, Synthesis, 1999, 603-606;
    • (1999) Synthesis , pp. 603-606
    • Kotsuki, H.1    Ohishi, T.2    Inoue, M.3    Kojima, T.4
  • 134
    • 26844571534 scopus 로고    scopus 로고
    • Scandium(III) trifluoromethanesulfonate-catalyzed Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates
    • H. Kotsuki, T. Ohishi and M. Inoue, Scandium(III) trifluoromethanesulfonate-catalyzed Friedel-Crafts alkylation of aromatic compounds with secondary alcohol methanesulfonates, Synlett, 1998, 255-256;
    • (1998) Synlett , pp. 255-256
    • Kotsuki, H.1    Ohishi, T.2    Inoue, M.3
  • 135
    • 37049062782 scopus 로고
    • Alkylation of the aromatic nucleus. I. The introduction of sec-alkyl and cyclohcxyl groups by reaction with esters of p-toluenesulfonic acid
    • W. J. Hickinbottom and N. W. Rogers, Alkylation of the aromatic nucleus. I. The introduction of sec-alkyl and cyclohcxyl groups by reaction with esters of p-toluenesulfonic acid, J. Chem. Soc., 1957, 4124-4130.
    • (1957) J. Chem. Soc. , pp. 4124-4130
    • Hickinbottom, W.J.1    Rogers, N.W.2
  • 136
    • 84984185547 scopus 로고
    • Proton magnetic resonance studies of internal rotation. VIII. Conformational analysis of α,α,o,o′-tetrasubstituted toluenes by nuclear magnetic resonance and semiempirical energy calculations
    • (a) A. Mannschreck and L. Ernst, Proton magnetic resonance studies of internal rotation. VIII. Conformational analysis of α,α,o,o′- tetrasubstituted toluenes by nuclear magnetic resonance and semiempirical energy calculations, Chem. Ber., 1971, 104, 228-247;
    • (1971) Chem. Ber. , vol.104 , pp. 228-247
    • Mannschreck, A.1    Ernst, L.2
  • 137
    • 0011492020 scopus 로고
    • Organic synthesis by electrolysis. VI. Anodic oxidation of arylcyclopropanes
    • (b) T. Shono and Y. Matsumura, Organic synthesis by electrolysis. VI. Anodic oxidation of arylcyclopropanes, J. Org. Chem., 1970, 35, 4157-4160.
    • (1970) J. Org. Chem. , vol.35 , pp. 4157-4160
    • Shono, T.1    Matsumura, Y.2
  • 138
    • 19744362309 scopus 로고
    • Strained benzene derivatives by copper-catalyzed tert-butylation
    • H. Kuenzer and S. Berger, Strained benzene derivatives by copper-catalyzed tert-butylation, J. Org. Chem., 1985, 50, 3222-3223.
    • (1985) J. Org. Chem. , vol.50 , pp. 3222-3223
    • Kuenzer, H.1    Berger, S.2
  • 139
    • 0000887799 scopus 로고
    • A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer
    • (a) C. G. Hatchard and C. A. Parker, A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer, Proc. R. Soc. London, A, 1956, 235, 518-536;
    • (1956) Proc. R. Soc. London, A , vol.235 , pp. 518-536
    • Hatchard, C.G.1    Parker, C.A.2
  • 142
    • 84946362024 scopus 로고
    • Application of unitary group methods for configuration interaction calculations
    • (a) D. Hegarty and M. A. Robb, Application of unitary group methods for configuration interaction calculations, Mol. Phys., 1979, 38, 1795-1812;
    • (1979) Mol. Phys. , vol.38 , pp. 1795-1812
    • Hegarty, D.1    Robb, M.A.2
  • 143
    • 4244069995 scopus 로고
    • A simple MC SCF perturbation theory: Orthogonal valence bond Moller-Plesset 2 (OVB MP2)
    • (b) J. J. W. McDouall, K. Peasley and M. A. Robb, A simple MC SCF perturbation theory: Orthogonal valence bond Moller-Plesset 2 (OVB MP2), Chem. Phys. Lett., 1988, 148, 183-189;
    • (1988) Chem. Phys. Lett. , vol.148 , pp. 183-189
    • McDouall, J.J.W.1    Peasley, K.2    Robb, M.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.