메뉴 건너뛰기




Volumn 113, Issue 21, 1991, Pages 8062-8069

Acylation of Alkenes Generated in Situ by Hydride Transfer from Isoalkanes. Synthesis of Pentalenones, Hydrindenones, and Cyclopentenones

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0001753423     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00021a036     Document Type: Article
Times cited : (23)

References (74)
  • 1
    • 0042504943 scopus 로고
    • Friedel-Crafts and Related Reactions
    • Olah, G. A., Ed.; Interscience: New York, Part 2.
    • Nenitzescu, C. D.; Balaban, A. T. In Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Interscience: New York, 1964; Vol. 3, Part 2, p 1033.
    • (1964) , vol.3 , pp. 1033
    • Nenitzescu, C.D.1    Balaban, A.T.2
  • 2
    • 0039316897 scopus 로고
    • Carbonium tons
    • Olah, G. A., Schleyer, P. von R., Eds.; Wiley-Interscience: New York.
    • Nenitzescu, C. D. In Carbonium tons; Olah, G. A., Schleyer, P. von R., Eds.; Wiley-Interscience: New York, 1970; p 463.
    • (1970) , pp. 463
    • Nenitzescu, C.D.1
  • 5
    • 0000194476 scopus 로고
    • For leading recent references concerning the hydride-transfer reaction in solution, see
    • For leading recent references concerning the hydride-transfer reaction in solution, see: (a) Kramer, G. M. Tetrahedron 1986, 42, 1071.
    • (1986) Tetrahedron , vol.42 , pp. 1071
    • Kramer, G.M.1
  • 12
    • 0008816704 scopus 로고
    • For a discussion on the transition state, see, and references therein.
    • For a discussion on the transition state, see: Karabatsos, G. J.; Tornaritis, M. Tetrahedron Lett. 1989, 30, 5733 and references therein.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5733
    • Karabatsos, G.J.1    Tornaritis, M.2
  • 16
    • 85022254449 scopus 로고
    • Studies by 27,A1 NMR have shown that the association of A1CI3 with acetyl chloride in CH2Cl2 solution gives only the donor-acceptor complex and not an ion pair including acylium ion; see
    • Studies by 27,A1 NMR have shown that the association of A1CI3 with acetyl chloride in CH2Cl2 solution gives only the donor-acceptor complex and not an ion pair including acylium ion; see: Wilinski, J.; Kurland, R. J. J. Am. Chem. Soc. 1978, 100, 2233.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 2233
    • Wilinski, J.1    Kurland, R.J.2
  • 21
    • 0001196105 scopus 로고
    • Acetylation of excess cyclohexane in the presence of AIC13 results in the formation of l-acetyl-2-methylcyclopentane as the main product; see
    • Acetylation of excess cyclohexane in the presence of AIC13 results in the formation of l-acetyl-2-methylcyclopentane as the main product; see: Vol’pin, M.; Akhrem, I.; Orlinkov, A. New J. Chem. 1989, 13, 771.
    • (1989) New J. Chem. , vol.13 , pp. 771
    • Vol’pin, M.1    Akhrem, I.2    Orlinkov, A.3
  • 22
    • 0002657031 scopus 로고
    • 1-Methyl-1-cyclopentyl cation was generated in superacid medium from cyclohexyl- or cyclopentyl-type precursors, see
    • 1-Methyl-1-cyclopentyl cation was generated in superacid medium from cyclohexyl- or cyclopentyl-type precursors, see: (a) Olah, G. A. Top. Curr. Chem. 1979, 80, 19.
    • (1979) Top. Curr. Chem. , vol.80 , pp. 19
    • Olah, G.A.1
  • 23
    • 33845183569 scopus 로고
    • This tertiary cation shows high stability in strong acid solutions, although both carbon and hydrogen scrambling occurs; see ref 2c, p 84.
    • Vancik, H.; Sunko, D. E. J. Am. Chem. Soc. 1989, 111, 3742. This tertiary cation shows high stability in strong acid solutions, although both carbon and hydrogen scrambling occurs; see ref 2c, p 84.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3742
    • Vancik, H.1    Sunko, D.E.2
  • 25
    • 18844437031 scopus 로고
    • Three mechanisms have been invoked to account for the acylation of olefins. Electrophilic attack
    • Three mechanisms have been invoked to account for the acylation of olefins. Electrophilic attack: (a) Beak, P.; Berger, K. R. J. Am. Chem. Soc. 1980, 102, 3848.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 3848
    • Beak, P.1    Berger, K.R.2
  • 27
    • 0002374799 scopus 로고
    • Cyclic transfer of the γ-hydrogen to oxygen
    • Cyclic transfer of the γ-hydrogen to oxygen: Groves, J. K. Chem. Soc. Rev. 1972, 1, 73.
    • (1972) Chem. Soc. Rev. , vol.1 , pp. 73
    • Groves, J.K.1
  • 29
    • 84918368901 scopus 로고
    • Diacetylation of 1-methyl-1-cyclohexene by Ac20-ZnCl2 occurs via acylation of the dienolate of 2-methyl-1 -acetyl- 1-cyclohexene
    • Diacetylation of 1-methyl-1-cyclohexene by Ac20-ZnCl2 occurs via acylation of the dienolate of 2-methyl-1 -acetyl- 1-cyclohexene; see: Dubois, M.; Cazaux, M. Bull. Soc. Chim. Fr. 1975, 274.
    • (1975) Bull. Soc. Chim. Fr. , pp. 274
    • Dubois, M.1    Cazaux, M.2
  • 30
    • 33845347239 scopus 로고
    • Advances in Heterocyclic Chemistry
    • Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York.
    • Diacetylation of acyclic alkenes leads to pyrylium salts; see: Balaban, A. T.; Schroth, W.; Fischer, G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1969; Vol. 10, p 241.
    • (1969) , vol.10 , pp. 241
    • Balaban, A.T.1    Schroth, W.2    Fischer, G.3
  • 32
    • 0042872229 scopus 로고
    • The alkylation of benzene also occurs selectively with cis-decalin; see
    • The alkylation of benzene also occurs selectively with cis-decalin; see: Ndandji, C.; Tsuchiya-Aikawa, L.; Gallo, R.; Metzger, J. Nouv. J. Chim. 1982, 6, 137.
    • (1982) Nouv. J. Chim. , vol.6 , pp. 137
    • Ndandji, C.1    Tsuchiya-Aikawa, L.2    Gallo, R.3    Metzger, J.4
  • 40
    • 0019462050 scopus 로고
    • Pentalenone 8a has been used in syntheses of propellane sesquiterpenes; see
    • Pentalenone 8a has been used in syntheses of propellane sesquiterpenes; see: (a) Schostarez, H.; Paquette, L. A. J. Am. Chem. Soc. 1981, 103, 722.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 722
    • Schostarez, H.1    Paquette, L.A.2
  • 43
    • 0042797088 scopus 로고
    • Mixtures of AlCl3 and cupric sulfate are known to be active for the isomerization of paraffins at room temperature; see ref 2c, p 56 and
    • Mixtures of AlCl3 and cupric sulfate are known to be active for the isomerization of paraffins at room temperature; see ref 2c, p 56 and Ono, Y.; Yamaguchi, K.; Kitajima, N. J. Catal. 1980, 64, 13.
    • (1980) J. Catal. , vol.64 , pp. 13
    • Ono, Y.1    Yamaguchi, K.2    Kitajima, N.3
  • 44
    • 85077851569 scopus 로고
    • For a review on the Nazarov cyclization, see
    • For a review on the Nazarov cyclization, see: Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429.
    • (1983) Synthesis , pp. 429
    • Santelli-Rouvier, C.1    Santelli, M.2
  • 45
    • 85077851569 scopus 로고
    • For a review on the Nazarov cyclization, see
    • For a review on the Nazarov cyclization, see: Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429.
    • (1983) Synthesis , pp. 429
    • Santelli-Rouvier, C.1    Santelli, M.2
  • 48
    • 84987344402 scopus 로고
    • For an example of methyl migration during a protic catalyzed Nazarov cyclization, see
    • For an example of methyl migration during a protic catalyzed Nazarov cyclization, see: Ohloff, G.; Schutte-Elte, K. H.; Demole, E. Helo. Chim. Acta 1971, 54, 2913.
    • (1971) Helo. Chim. Acta , vol.54 , pp. 2913
    • Ohloff, G.1    Schutte-Elte, K.H.2    Demole, E.3
  • 49
    • 0005427308 scopus 로고
    • Tertiary cycloalkyl cations frequently undergo ring expansion or contraction; see
    • Tertiary cycloalkyl cations frequently undergo ring expansion or contraction; see: Kirchen, R. P.; Sorensen, T. S.; Wagstaff, K. E. J. Am. Chem. Soc. 1978, 100, 5134.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5134
    • Kirchen, R.P.1    Sorensen, T.S.2    Wagstaff, K.E.3
  • 51
    • 0024538847 scopus 로고
    • It is well-known that the effect of the replacement of hydrogen by deuterium on the proton noise-decoupled 13C NMR spectrum is to reduce the intensity of the signal due to the carbon bearing the deuterium; for examples, see
    • It is well-known that the effect of the replacement of hydrogen by deuterium on the proton noise-decoupled 13C NMR spectrum is to reduce the intensity of the signal due to the carbon bearing the deuterium; for examples, see: Brownstein, S.; Burton, G. W.; Hughes, L.; Ingold, K. U. J. Org. Chem. 1989, 54, 560.
    • (1989) J. Org. Chem. , vol.54 , pp. 560
    • Brownstein, S.1    Burton, G.W.2    Hughes, L.3    Ingold, K.U.4
  • 52
    • 85022930356 scopus 로고
    • The 2-methyl-2-butyl cation shows degenerate properties with interchange of the two types of methyl group protons, not affecting the methylene group. For a review, see
    • The 2-methyl-2-butyl cation shows degenerate properties with interchange of the two types of methyl group protons, not affecting the methylene group. For a review, see: Ahlberg, P.; Jonsall, G.; Engdahl, C. Adv. Phys. Org. Chem. 1988, 19, 223.
    • (1988) Adv. Phys. Org. Chem. , vol.19 , pp. 223
    • Ahlberg, P.1    Jonsall, G.2    Engdahl, C.3
  • 53
    • 0003869278 scopus 로고
    • The Conservation of Orbital Symmetry
    • Verlag Chemie-Academic Press: Weinheim.
    • Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie-Academic Press: Weinheim, 1970; p 58.
    • (1970) , pp. 58
    • Woodward, R.B.1    Hoffmann, R.2
  • 55
    • 0003869278 scopus 로고
    • The Conservation of Orbital Symmetry
    • Verlag Chemie-Academic Press: Weinheim.
    • Woodward, R. B.; Hoffmann, R. The Conservation of Orbital Symmetry; Verlag Chemie-Academic Press: Weinheim, 1970; p 128.
    • (1970) , pp. 128
    • Woodward, R.B.1    Hoffmann, R.2
  • 60
    • 33847801683 scopus 로고
    • In the same way, the chain elongation observed by treatment in acidic medium of 2,3-dimethyl-4-penten-2-ol could result from a methyl 1,4-migration; see
    • In the same way, the chain elongation observed by treatment in acidic medium of 2,3-dimethyl-4-penten-2-ol could result from a methyl 1,4-migration; see: Deno, N. C.; Lastomirsky, R. R. J. Org. Chem. 1975, 40, 514.
    • (1975) J. Org. Chem. , vol.40 , pp. 514
    • Deno, N.C.1    Lastomirsky, R.R.2
  • 61
    • 0001635002 scopus 로고
    • Methyl 1,4-migrations have been invoked in Fischer indole cylizations; see
    • Methyl 1,4-migrations have been invoked in Fischer indole cylizations; see: (a) Miller, B.; Matjeka, E. R. J. Am. Chem. Soc. 1980, 102, 4772.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4772
    • Miller, B.1    Matjeka, E.R.2
  • 64
    • 33845560254 scopus 로고
    • In rearrangement of β-naphtalenones, see
    • Miller, B.; Lin, W.-O. J. Org. Chem. 1979, 44, 887. In rearrangement of β-naphtalenones, see
    • (1979) J. Org. Chem. , vol.44 , pp. 887
    • Miller, B.1    Lin, W.-O.2
  • 66
    • 33845560254 scopus 로고
    • In rearrangement of 4,4-disubstituted-2-cyclohexenols, see
    • Miller, B.; Lin, W.-O. J. Org. Chem. 1979, 44, 887. In rearrangement of 4,4-disubstituted-2-cyclohexenols, see
    • (1979) J. Org. Chem. , vol.44 , pp. 887
    • Miller, B.1    Lin, W.-O.2
  • 68
    • 0004231256 scopus 로고
    • Pericyclic Reactions
    • In rearrangements of bicyclo[3.1.0]hexenyl carbonium ions, see, Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York.
    • In rearrangements of bicyclo[3.1.0]hexenyl carbonium ions, see: Sorensen, T. S.; Rauk, A. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. 11, p 59.
    • (1977) , vol.11 , pp. 59
    • Sorensen, T.S.1    Rauk, A.2
  • 70
    • 0007170126 scopus 로고
    • For examples of fragmentation reactions in superacid medium, see
    • For examples of fragmentation reactions in superacid medium, see: Karabatsos, G. J.; Vane, F. M.; Meyerson, S. J. Am. Chem. Soc. 1963, 85, 733.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 733
    • Karabatsos, G.J.1    Vane, F.M.2    Meyerson, S.3
  • 71
    • 0003467672 scopus 로고
    • Advanced Organic Chemistry
    • For examples of the slow delivery of bromine from NBS, see, J. Wiley & Sons: New York. For examples of the in situ preparation of Grignard reagents (Barbier reaction), see
    • For examples of the slow delivery of bromine from NBS, see: March, J. Advanced Organic Chemistry; J. Wiley & Sons: New York, 1985; p 625. For examples of the in situ preparation of Grignard reagents (Barbier reaction), see
    • (1985) , pp. 625
    • March, J.1
  • 73
    • 0041906332 scopus 로고
    • For examples of the in situ formation of methyl vinyl ketone in the Robinson annulation reaction, see
    • For examples of the in situ formation of methyl vinyl ketone in the Robinson annulation reaction, see: Jung, M. E. Tetrahedron 1976, 32, 1.
    • (1976) Tetrahedron , vol.32 , pp. 1
    • Jung, M.E.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.