메뉴 건너뛰기




Volumn 118, Issue 33, 1996, Pages 7716-7730

Hypervalent (tert-butylperoxy)iodanes generate iodine-centered radicals at room temperature in solution: Oxidation and deprotection of benzyl and allyl ethers, and evidence for generation of α-oxy carbon radicals

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; ETHER DERIVATIVE;

EID: 0029840740     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9610287     Document Type: Article
Times cited : (131)

References (163)
  • 1
    • 33947337456 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1966) Chem. Rev. , vol.66 , pp. 243
    • Banks, D.F.1
  • 2
    • 0003590349 scopus 로고
    • Wiley: New York, Chapter 18
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1983) The Chemistry of Functional Groups, Supplemented D
    • Koser, G.F.1
  • 3
    • 0021127516 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1984) Synthesis , pp. 709
    • Varvoglis, A.1
  • 4
    • 0022756366 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1986) J. Synth. Org. Chem., Jpn. , vol.44 , pp. 660
    • Ochiai, M.1    Nagao, Y.2
  • 5
    • 33845375869 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 244
    • Moriarty, R.M.1    Prakash, O.2
  • 6
    • 0842298066 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1987) Russ. Chem. Rev. , vol.56 , pp. 826
    • Merkushev, E.B.1
  • 7
    • 0002121681 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1989) Revs. Heteroatom Chem. , vol.2 , pp. 92
    • Ochiai, M.1
  • 8
    • 85033148217 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1990) Synthesis , pp. 431
    • Moriarty, R.M.1    Vaid, R.K.2
  • 9
    • 85022481701 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1990) Synlett. , pp. 365
    • Moriarty, R.M.1    Vaid, R.K.2    Koser, G.F.3
  • 10
    • 33748231777 scopus 로고
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 274
    • Stang, P.J.1
  • 11
    • 0003410653 scopus 로고
    • VHC Publishers: New York
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1992) The Chemistry of Polycoordinated Iodine
    • Varvoglis, A.1
  • 12
    • 0003590349 scopus 로고
    • Wiley: New York, Chapter 21
    • For reviews of organoiodanes, see: (a) Banks, D. F. Chem. Rev. 1966, 66, 243. (b) Koser, G. F. The Chemistry of Functional Groups, Supplemented D; Wiley: New York, 1983; Chapter 18. (c) Varvoglis, A. Synthesis 1984, 709. (d) Ochiai, M.; Nagao, Y. J. Synth. Org. Chem., Jpn. 1986, 44, 660. (e) Moriarty, R. M.; Prakash, O. Acc. Chem. Res. 1986, 19, 244. (f) Merkushev, E. B. Russ. Chem. Rev. 1987, 56, 826. (g) Ochiai, M. Revs. Heteroatom Chem. 1989, 2, 92. (h) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (i) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett. 1990, 365. (j) Stang, P. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 274. (k) Varvoglis, A. The Chemistry of Polycoordinated Iodine. VHC Publishers: New York, 1992. (l) Koser, G. F. The Chemistry of Functional Groups, Supplement D2; Wiley: New York, 1995; Chapter 21.
    • (1995) The Chemistry of Functional Groups, Supplement D2
    • Koser, G.F.1
  • 20
    • 0001590559 scopus 로고
    • Moss and Zhang also reported a synthesis of the peroxyiodane 1a involving a ligand exchange of a labile (phosphoryloxy)iodane, prepared in situ by the reaction of 1-chloro-1,2-benziodoxol-3(1H)-one with silver diphenyl phosphate in DMSO, with tert-butyl hydroperoxide. See: Moss, R. A.; Zhang, H. J. Am. Chem. Soc. 1994, 116, 4471.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4471
    • Moss, R.A.1    Zhang, H.2
  • 27
  • 28
    • 0010403626 scopus 로고
    • 3: Hirama, M.; Shimizu, M. Synth. Commun. 1983, 13, 781. Angibeaud, P.; Defaye, J.; Gadelle, A.; Utille, J.-P. Synthesis 1985, 1123.
    • (1983) Synth. Commun. , vol.13 , pp. 781
    • Hirama, M.1    Shimizu, M.2
  • 39
    • 9444277026 scopus 로고
    • Benzoic acid formed has been shown to decompose the hydroperoxide product. See: Tunoda, Y.; Matumoto, Y. Kogyo Kagaku Zasshi 1959, 62, 1555.
    • (1959) Kogyo Kagaku Zasshi , vol.62 , pp. 1555
    • Tunoda, Y.1    Matumoto, Y.2
  • 40
    • 0001412888 scopus 로고
    • 3, which could scavenge the hydrogen bromide produced in the reactions. For this bromination, both the trichloromethyl radical and the bromine atom, generated from hydrogen bromide, have been suggested to participate in benzylic hydrogen atom abstraction. See: (a) Tanner, D. D.; Arhart, R. J.; Blackburn, E. V.; Das, N. C.; Wada, N. J. Am. Chem. Soc. 1974, 96, 829. (b) Tanner, D. D.; Wada, N. J. Am. Chem. Soc. 1975, 97, 2190. (c) Krosley, K. W.; Gleicher, G. J. J. Org. Chem. 1990, 55, 4469.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 829
    • Tanner, D.D.1    Arhart, R.J.2    Blackburn, E.V.3    Das, N.C.4    Wada, N.5
  • 41
    • 0344280794 scopus 로고
    • 3, which could scavenge the hydrogen bromide produced in the reactions. For this bromination, both the trichloromethyl radical and the bromine atom, generated from hydrogen bromide, have been suggested to participate in benzylic hydrogen atom abstraction. See: (a) Tanner, D. D.; Arhart, R. J.; Blackburn, E. V.; Das, N. C.; Wada, N. J. Am. Chem. Soc. 1974, 96, 829. (b) Tanner, D. D.; Wada, N. J. Am. Chem. Soc. 1975, 97, 2190. (c) Krosley, K. W.; Gleicher, G. J. J. Org. Chem. 1990, 55, 4469.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 2190
    • Tanner, D.D.1    Wada, N.2
  • 42
    • 0039892570 scopus 로고
    • 3, which could scavenge the hydrogen bromide produced in the reactions. For this bromination, both the trichloromethyl radical and the bromine atom, generated from hydrogen bromide, have been suggested to participate in benzylic hydrogen atom abstraction. See: (a) Tanner, D. D.; Arhart, R. J.; Blackburn, E. V.; Das, N. C.; Wada, N. J. Am. Chem. Soc. 1974, 96, 829. (b) Tanner, D. D.; Wada, N. J. Am. Chem. Soc. 1975, 97, 2190. (c) Krosley, K. W.; Gleicher, G. J. J. Org. Chem. 1990, 55, 4469.
    • (1990) J. Org. Chem. , vol.55 , pp. 4469
    • Krosley, K.W.1    Gleicher, G.J.2
  • 58
    • 9444234345 scopus 로고    scopus 로고
    • note
    • It is not at all clear whether or not the added p-methoxyphenol traps radicals generated in the reaction. We found that oxidation of phenols with the peroxyiodane 1a takes place, and the results will be reported elsewhere.
  • 59
    • 33845557804 scopus 로고
    • For peroxy radical-trapping with α-tocopherol, see: (a) Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6478. (b) Jackson, R. A.; Hosseini, K. M. J. Chem. Soc., Chem. Commun. 1992, 967.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6478
    • Barclay, L.R.C.1    Ingold, K.U.2
  • 60
    • 37049085722 scopus 로고
    • For peroxy radical-trapping with α-tocopherol, see: (a) Barclay, L. R. C.; Ingold, K. U. J. Am. Chem. Soc. 1981, 103, 6478. (b) Jackson, R. A.; Hosseini, K. M. J. Chem. Soc., Chem. Commun. 1992, 967.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 967
    • Jackson, R.A.1    Hosseini, K.M.2
  • 62
    • 9444272674 scopus 로고    scopus 로고
    • note
    • Furthermore, added galvinoxyl completely inhibits the oxidation of the allyl ether 6a.
  • 66
    • 0343043242 scopus 로고
    • For 5-exo cyclizations of 1-phenyl-5-hexenyl radicals, see: (a) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064. (b) Pines, H.; Sih, N. C.; Rosenfield, D. B. J. Org. Chem. 1966, 31, 2255.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6064
    • Walling, C.1    Cioffari, A.2
  • 67
    • 0000168669 scopus 로고
    • For 5-exo cyclizations of 1-phenyl-5-hexenyl radicals, see: (a) Walling, C.; Cioffari, A. J. Am. Chem. Soc. 1972, 94, 6064. (b) Pines, H.; Sih, N. C.; Rosenfield, D. B. J. Org. Chem. 1966, 31, 2255.
    • (1966) J. Org. Chem. , vol.31 , pp. 2255
    • Pines, H.1    Sih, N.C.2    Rosenfield, D.B.3
  • 68
    • 0001527994 scopus 로고
    • -1, respectively. See: (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Ha, C.; Horner, J. H.; Newcomb, M.; Varick, T. R.; Arnold, B. R.; Lusztyk, J. J. Org. Chem. 1993, 58, 1194. (c) Newcomb, M.; Horner, J. H.; Shahin, H. Tetrahedron Lett. 1993, 34, 5523.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 7739
  • 69
    • 0000955680 scopus 로고
    • -1, respectively. See: (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Ha, C.; Horner, J. H.; Newcomb, M.; Varick, T. R.; Arnold, B. R.; Lusztyk, J. J. Org. Chem. 1993, 58, 1194. (c) Newcomb, M.; Horner, J. H.; Shahin, H. Tetrahedron Lett. 1993, 34, 5523.
    • (1993) J. Org. Chem. , vol.58 , pp. 1194
    • Ha, C.1    Horner, J.H.2    Newcomb, M.3    Varick, T.R.4    Arnold, B.R.5    Lusztyk, J.6
  • 70
    • 0027161832 scopus 로고
    • -1, respectively. See: (a) Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 7739. (b) Ha, C.; Horner, J. H.; Newcomb, M.; Varick, T. R.; Arnold, B. R.; Lusztyk, J. J. Org. Chem. 1993, 58, 1194. (c) Newcomb, M.; Horner, J. H.; Shahin, H. Tetrahedron Lett. 1993, 34, 5523.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 5523
    • Newcomb, M.1    Horner, J.H.2    Shahin, H.3
  • 74
    • 0001513165 scopus 로고
    • On the other hand, the cyclization rate constants of 1-methoxy-5-hexenyl radicals have been shown to be nearly equal to those for related alkyl radicals lacking the methoxy group. See: (a) Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684. (b) Newcomb, M.; Filipkowski, M. A.; Johnson, C. C. Tetrahedron Lett. 1995, 36, 3643.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 1684
    • Johnson, C.C.1    Horner, J.H.2    Tronche, C.3    Newcomb, M.4
  • 75
    • 0029070009 scopus 로고
    • On the other hand, the cyclization rate constants of 1-methoxy-5-hexenyl radicals have been shown to be nearly equal to those for related alkyl radicals lacking the methoxy group. See: (a) Johnson, C. C.; Horner, J. H.; Tronche, C.; Newcomb, M. J. Am. Chem. Soc. 1995, 117, 1684. (b) Newcomb, M.; Filipkowski, M. A.; Johnson, C. C. Tetrahedron Lett. 1995, 36, 3643.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3643
    • Newcomb, M.1    Filipkowski, M.A.2    Johnson, C.C.3
  • 97
    • 0004032955 scopus 로고
    • Wiley: New York, Chapter 12
    • Howard, J. A. Free Radicals; Wiley: New York, 1973; Vol. 2, Chapter 12.
    • (1973) Free Radicals , vol.2
    • Howard, J.A.1
  • 99
    • 9444253931 scopus 로고    scopus 로고
    • note
    • 2b
  • 106
    • 33847805231 scopus 로고
    • Breslow and his co-workers developed the template-directed chlorination of steroids via generation of iodanyl radicals. See: (a) Breslow, R.; Corcoran, R.; Dale, J. A.; Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. (b) Breslow, R.; Corcoran, R. J.; Snider, B. B. J. Am. Chem. Soc. 1974, 96, 6791. (c) Breslow, R.; Snider, B. B.; Corcoran, R. J. J. Am. Chem. Soc. 1974, 96, 6794. (d) White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 1973
    • Breslow, R.1    Corcoran, R.2    Dale, J.A.3    Liu, S.4    Kalicky, P.5
  • 107
    • 0016395141 scopus 로고
    • Breslow and his co-workers developed the template-directed chlorination of steroids via generation of iodanyl radicals. See: (a) Breslow, R.; Corcoran, R.; Dale, J. A.; Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. (b) Breslow, R.; Corcoran, R. J.; Snider, B. B. J. Am. Chem. Soc. 1974, 96, 6791. (c) Breslow, R.; Snider, B. B.; Corcoran, R. J. J. Am. Chem. Soc. 1974, 96, 6794. (d) White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6791
    • Breslow, R.1    Corcoran, R.J.2    Snider, B.B.3
  • 108
    • 0016395141 scopus 로고
    • Breslow and his co-workers developed the template-directed chlorination of steroids via generation of iodanyl radicals. See: (a) Breslow, R.; Corcoran, R.; Dale, J. A.; Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. (b) Breslow, R.; Corcoran, R. J.; Snider, B. B. J. Am. Chem. Soc. 1974, 96, 6791. (c) Breslow, R.; Snider, B. B.; Corcoran, R. J. J. Am. Chem. Soc. 1974, 96, 6794. (d) White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6794
    • Breslow, R.1    Snider, B.B.2    Corcoran, R.J.3
  • 109
    • 0000615859 scopus 로고
    • Breslow and his co-workers developed the template-directed chlorination of steroids via generation of iodanyl radicals. See: (a) Breslow, R.; Corcoran, R.; Dale, J. A.; Liu, S.; Kalicky, P. J. Am. Chem. Soc. 1974, 96, 1973. (b) Breslow, R.; Corcoran, R. J.; Snider, B. B. J. Am. Chem. Soc. 1974, 96, 6791. (c) Breslow, R.; Snider, B. B.; Corcoran, R. J. J. Am. Chem. Soc. 1974, 96, 6794. (d) White, P.; Breslow, R. J. Am. Chem. Soc. 1990, 112, 6842.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6842
    • White, P.1    Breslow, R.2
  • 122
    • 9444272673 scopus 로고    scopus 로고
    • note
    • tert-Butylperoxy radical may also abstract benzylic hydrogens of 2d.
  • 123
    • 9444297708 scopus 로고    scopus 로고
    • note
    • 51
  • 124
    • 9444235519 scopus 로고
    • 34e See also: (a) Cass, W. E. J. Am. Chem. Soc. 1947, 69, 500. (b) Cass, W. E. J. Am. Chem. Soc. 1950, 72, 4915.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 500
    • Cass, W.E.1
  • 125
    • 9444295780 scopus 로고
    • 34e See also: (a) Cass, W. E. J. Am. Chem. Soc. 1947, 69, 500. (b) Cass, W. E. J. Am. Chem. Soc. 1950, 72, 4915.
    • (1950) J. Am. Chem. Soc. , vol.72 , pp. 4915
    • Cass, W.E.1
  • 126
    • 9444259048 scopus 로고    scopus 로고
    • note
    • 46 have been generally accepted.
  • 131
    • 9444285682 scopus 로고    scopus 로고
    • note
    • 43
  • 132
    • 33947090335 scopus 로고
    • Photoelectron spectroscopy shows that the oxidation potential of aromatic π electrons of benzyl ethers is lower than that of the nonbonding electrons on oxygen. Therefore, the charge density of benzyl ether cation radicals has been assumed to be located in the π system rather than localized on the potentially oxidizable oxygen atom. See: (a) Mayeda, E. A.; Miller, L. L.; Wolf, J. F. J. Am. Chem. Soc. 1972, 94, 6812. (b) Pincock, J. A.; Pincock, A. L.; Fox, M. A. Tetrahedron 1985, 41, 4107.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 6812
    • Mayeda, E.A.1    Miller, L.L.2    Wolf, J.F.3
  • 133
    • 0001073256 scopus 로고
    • Photoelectron spectroscopy shows that the oxidation potential of aromatic π electrons of benzyl ethers is lower than that of the nonbonding electrons on oxygen. Therefore, the charge density of benzyl ether cation radicals has been assumed to be located in the π system rather than localized on the potentially oxidizable oxygen atom. See: (a) Mayeda, E. A.; Miller, L. L.; Wolf, J. F. J. Am. Chem. Soc. 1972, 94, 6812. (b) Pincock, J. A.; Pincock, A. L.; Fox, M. A. Tetrahedron 1985, 41, 4107.
    • (1985) Tetrahedron , vol.41 , pp. 4107
    • Pincock, J.A.1    Pincock, A.L.2    Fox, M.A.3
  • 135
    • 84988073214 scopus 로고
    • Ionization potential calculated by MOPAC7: 2d, 9.42 eV; 2p, 8.90 eV; 2q, 9.17 eV; 2r, 9.18 eV; 2s, 9.30 eV. See: Steward, J. J. P. J. Comput. Chem. 1989, 10, 221.
    • (1989) J. Comput. Chem. , vol.10 , pp. 221
    • Steward, J.J.P.1
  • 136
    • 9444228079 scopus 로고    scopus 로고
    • note
    • 9g
  • 140
    • 0002080422 scopus 로고
    • Using the technique of time-resolved microwave dielectric absorption, the dipole moment of benzylperoxy radical has been reported to be 2.4 ± 0.2 D. See: Fessenden, R. W.; Hitachi, A.; Nagarajan, V. J. Phys. Chem. 1984, 88, 107.
    • (1984) J. Phys. Chem. , vol.88 , pp. 107
    • Fessenden, R.W.1    Hitachi, A.2    Nagarajan, V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.