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Volumn 60, Issue 3, 1995, Pages 703-710

1,3-Diselenetanes and 1,3-Dithietanes Derived from Camphor. Formation, Structure, Stereochemistry, and Oxidation to Selenoxide and Sulfoxide Products

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EID: 33751154842     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00108a038     Document Type: Article
Times cited : (82)

References (49)
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    • A selenium substituent in the a-position of a ketone stabilizes the conjugate base and so increases the acidity of the a-hydrogen atom. See
    • A selenium substituent in the a-position of a ketone stabilizes the conjugate base and so increases the acidity of the a-hydrogen atom. See: Reich, H. J. Acc. Chem. Res. 1979, 12, 22.
    • (1979) Acc. Chem. Res. , vol.12 , pp. 22
    • Reich, H.J.1
  • 18
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    • For reviews of selones and related selenocarbonyl compounds, see: (a) Liotta, D., Ed.; Wiley: Chichester Chapter 6
    • For reviews of selones and related selenocarbonyl compounds, see: (a) Guziec, F. S., Jr. In Organoselenium Chemistry, Liotta, D., Ed.; Wiley: Chichester, 1987; Chapter 6.
    • (1987) Organoselenium Chemistry
    • Guziec, F.S.1
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    • For examples of related a- to a'-transselenenylations to ketone enolates, see: (a)
    • For examples of related a- to a'-transselenenylations to ketone enolates, see: (a) Liotta, D.; Saindane, M.; Brothers, D. J. Org. Chem. 1982, 47, 1598.
    • (1982) J. Org. Chem. , vol.47 , pp. 1598
    • Liotta, D.1    Saindane, M.2    Brothers, D.3
  • 23
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    • For a general discussion of these processes, see: (b) Liotta, D., Ed.; Wiley: Chichester Chapter 1
    • For a general discussion of these processes, see: (b) Back, T. G. In Organoselenium Chemistry, Liotta, D., Ed.; Wiley: Chichester, 1987; Chapter 1.
    • (1987) Organoselenium Chemistry
    • Back, T.G.1
  • 24
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    • For examples of trapping of selenoketones and selenoaldehydes with 1,3-dienes, see: (a)
    • For examples of trapping of selenoketones and selenoaldehydes with 1,3-dienes, see: (a) Kirby, G. W.; Trethewey, A. N., J. Chem. Soc Chem. Commun. 1986, 1152.
    • (1986) J. Chem. Soc Chem. Commun. , pp. 1152
    • Kirby, G.W.1    Trethewey, A.N.2
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    • The dimerizations of thioketones and related compounds have been known for many years: (a)
    • The dimerizations of thioketones and related compounds have been known for many years: (a) SchSnberg, A.; Stephenson, A. Chem. Ber. 1933, 66, 567.
    • (1933) Chem. Ber. , vol.66 , pp. 567
    • SchSnberg, A.1    Stephenson, A.2
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    • For examples of these and related cycloadditions, see: (b) Academic Press: New York Chapter 7
    • For examples of these and related cycloadditions, see: (b) Block, E. In Reactions of Organosulfur Compounds, Academic Press: New York, 1978; Chapter 7, pp 278-280.
    • (1978) Reactions of Organosulfur Compounds , pp. 278-280
    • Block, E.1
  • 34
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    • The mechanism for the dimerization of adamantanethione under photochemical conditions has been studied in detail: (a)
    • The mechanism for the dimerization of adamantanethione under photochemical conditions has been studied in detail: (a) Lawrence, A. H.; Liao, C. C.; de Mayo, P.; Ramamurthy, V. J. Am. Chem. Soc. 1976, 98, 3572.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 3572
    • Lawrence, A.H.1    Liao, C.C.2    de Mayo, P.3    Ramamurthy, V.4
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    • However, detailed mechanistic studies of the dimerization of other thio- and selenocarbonyl compounds appear to be lacking
    • Greidanus, J. W. Can. J. Chem. 1970, 48, 3530. However, detailed mechanistic studies of the dimerization of other thio- and selenocarbonyl compounds appear to be lacking.
    • (1970) Can. J. Chem. , vol.48 , pp. 3530
    • Greidanus, J.W.1
  • 37
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    • The downfield shift of H(4) in both camphor moieties (from 6 2.53 in 21 to 5 2.84 and 5 2.71 and 24) and of the endo-H(5) proton on one camphor unit (from d 1.88 to ó 2.58) is attributed to their location in the deshielding zone of the sulfoxide bond. For examples of similar effects caused by acetylene-like anisotropy of sulfoxides, see: (a)
    • The downfield shift of H(4) in both camphor moieties (from 6 2.53 in 21 to 5 2.84 and 5 2.71 and 24) and of the endo-H(5) proton on one camphor unit (from d 1.88 to ó 2.58) is attributed to their location in the deshielding zone of the sulfoxide bond. For examples of similar effects caused by acetylene-like anisotropy of sulfoxides, see: (a) Buck, K. W.; Foster, A. B.; Pardoe, W. D., Qadir, M. H.; Webber, J. M. J. Chem. Soc., Chem. Commun. 1966, 759.
    • (1966) J. Chem. Soc., Chem. Commun. , pp. 759
    • Buck, K.W.1    Foster, A.B.2    Pardoe, W.D.3    Qadir, M.H.4    Webber, J.M.5
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    • Horning, E. C, Ed.; Wiley: New York Collect.
    • Lucas, H. J.; Kennedy, E. R.; Formo, M. W. In Organic Syntheses, Horning, E. C, Ed.; Wiley: New York, 1955; Collect. Vol. Ill, p 483.
    • (1955) Organic Syntheses , vol.Ill , pp. 483
    • Lucas, H.J.1    Kennedy, E.R.2    Formo, M.W.3
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.