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Volumn 119, Issue 48, 1997, Pages 11598-11604

Generation and reaction of monocarbonyliodonium ylides: Ester exchange of (Z)-(β-acetoxyvinyl)iodonium salts with lithium ethoxide and synthesis of α,β-epoxy ketones

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; KETONE;

EID: 0031439297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971688r     Document Type: Article
Times cited : (51)

References (41)
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    • Wiley: New York, Chapter 18
    • For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18. (b) Varvoglis, A. Synthesis 1984, 709. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (d) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VHC Publishers: New York, 1992; Chapter 6. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1983) The Chemistry of Functional Groups, Supplement D
    • Koser, G.F.1
  • 2
    • 0021127516 scopus 로고
    • For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18. (b) Varvoglis, A. Synthesis 1984, 709. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (d) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VHC Publishers: New York, 1992; Chapter 6. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1984) Synthesis , pp. 709
    • Varvoglis, A.1
  • 3
    • 85033148217 scopus 로고
    • For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18. (b) Varvoglis, A. Synthesis 1984, 709. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (d) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VHC Publishers: New York, 1992; Chapter 6. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1990) Synthesis , pp. 431
    • Moriarty, R.M.1    Vaid, R.K.2
  • 4
    • 0003410653 scopus 로고
    • VHC Publishers: New York, Chapter 6
    • For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18. (b) Varvoglis, A. Synthesis 1984, 709. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (d) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VHC Publishers: New York, 1992; Chapter 6. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1992) The Chemistry of Polycoordinated Iodine
    • Varvoglis, A.1
  • 5
    • 0001213492 scopus 로고    scopus 로고
    • For reviews of iodonium ylides, see: (a) Koser, G. F. The Chemistry of Functional Groups, Supplement D; Wiley: New York, 1983; Chapter 18. (b) Varvoglis, A. Synthesis 1984, 709. (c) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (d) Varvoglis, A. The Chemistry of Polycoordinated Iodine; VHC Publishers: New York, 1992; Chapter 6. (e) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
    • (1996) Chem. Rev. , vol.96 , pp. 1123
    • Stang, P.J.1    Zhdankin, V.V.2
  • 9
    • 0010029513 scopus 로고
    • Transient formation of unstabilized iodonium ylides has been proposed to occur by hydrogen-deuterium exchange. See: (a) Olah, G. A.; Yamada, Y.; Spear, R. J. J. Am. Chem. Soc. 1975, 97, 680. (b) Stang, P. J.; Wingert, H.; Arif, A. M. J. Am. Chem. Soc. 1987, 709, 7235. (c) Ochiai, M.; Kunishima, M.; Fuji, K.; Shiro, M.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1988, 1076.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 680
    • Olah, G.A.1    Yamada, Y.2    Spear, R.J.3
  • 10
    • 33845283442 scopus 로고
    • Transient formation of unstabilized iodonium ylides has been proposed to occur by hydrogen-deuterium exchange. See: (a) Olah, G. A.; Yamada, Y.; Spear, R. J. J. Am. Chem. Soc. 1975, 97, 680. (b) Stang, P. J.; Wingert, H.; Arif, A. M. J. Am. Chem. Soc. 1987, 709, 7235. (c) Ochiai, M.; Kunishima, M.; Fuji, K.; Shiro, M.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1988, 1076.
    • (1987) J. Am. Chem. Soc. , vol.709 , pp. 7235
    • Stang, P.J.1    Wingert, H.2    Arif, A.M.3
  • 11
    • 37049068824 scopus 로고
    • Transient formation of unstabilized iodonium ylides has been proposed to occur by hydrogen-deuterium exchange. See: (a) Olah, G. A.; Yamada, Y.; Spear, R. J. J. Am. Chem. Soc. 1975, 97, 680. (b) Stang, P. J.; Wingert, H.; Arif, A. M. J. Am. Chem. Soc. 1987, 709, 7235. (c) Ochiai, M.; Kunishima, M.; Fuji, K.; Shiro, M.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1988, 1076.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 1076
    • Ochiai, M.1    Kunishima, M.2    Fuji, K.3    Shiro, M.4    Nagao, Y.5
  • 28
    • 17344369515 scopus 로고    scopus 로고
    • Vinyliodanes with similar cyclic structure have been reported. See ref 3b
    • Vinyliodanes with similar cyclic structure have been reported. See ref 3b.
  • 31
    • 17344363165 scopus 로고    scopus 로고
    • 1H NMR spectra of ylides 2b, 2b-αd, and 2c are included as Supporting Information (Figures S1-S3)
    • 1H NMR spectra of ylides 2b, 2b-αd, and 2c are included as Supporting Information (Figures S1-S3).
  • 32
    • 17344361801 scopus 로고    scopus 로고
    • note
    • 4,5
  • 41
    • 17344372739 scopus 로고
    • Temnikova, T. I.; Kropachev, V. A. Zh. Obshch. Khim. 1948, 18, 692; Chem. Abstr. 1949, 43, 139c.
    • (1949) Chem. Abstr. , vol.43


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