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Volumn 63, Issue 5, 1998, Pages 1724-1726

A new synthesis of selenol esters via carbophilic addition of organocopper reagents to carbonyl selenide

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EID: 0001089561     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9717189     Document Type: Note
Times cited : (18)

References (78)
  • 2
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    • Thiocarboxylation towards carbon nucleophiles such as enolates (a, b), phosphorous ylides (c), and an acyllithium (d). (a) Demuynck, C.; Thullier, A. Bull. Soc. Chim. Fr. 1969, 2434.
    • (1969) Bull. Soc. Chim. Fr. , pp. 2434
    • Demuynck, C.1    Thullier, A.2
  • 6
    • 0001283330 scopus 로고
    • Thiocarboxylation towards heteroatom nucleophiles such as alcoholates (a), phenolates (b), and amines (a). (a) Ferm, R. J. Chem. Rev. 1957, 57, 621.
    • (1957) Chem. Rev. , vol.57 , pp. 621
    • Ferm, R.J.1
  • 8
    • 39749105477 scopus 로고
    • Chem. Abstr 1991, 115, 28833r.
    • (1991) Chem. Abstr , vol.115
  • 11
    • 61849087291 scopus 로고    scopus 로고
    • note
    • 16 react at the sulfur atom.
  • 22
    • 0001922323 scopus 로고
    • Reactions of dithioesters with organolithium and Grignard reagents proceed in a thiophilic manner: (a) Léger, L.; Saquet, M. Bull. Soc. Chim. Fr. 1975, 657.
    • (1975) Bull. Soc. Chim. Fr. , pp. 657
    • Léger, L.1    Saquet, M.2
  • 28
    • 0000202984 scopus 로고
    • Reactions of dithioesters with allyl, benzyl, propagyl, and vinyl Grignard reagents proceed in a carbophilic manner: (g) Masson, S.; Saquet, M.; Thuillier, A. Tetrahedron 1977, 33, 2949.
    • (1977) Tetrahedron , vol.33 , pp. 2949
    • Masson, S.1    Saquet, M.2    Thuillier, A.3
  • 57
    • 61849148853 scopus 로고    scopus 로고
    • note
    • 23
  • 67
    • 61849116809 scopus 로고    scopus 로고
    • note
    • The reaction of SCO with PhLi was examined in detail in order to compare the reactivities of SeCO and SCO. Thus, SCO was treated with PhLi under identical conditions as in run 1 of Table 1 by using MeI instead of BzBr; the corresponding thiol ester 3 was obtained in 95% yield via carbophilic attack without any thiophilic products (eq (Formula Presented)
  • 69
    • 61849102397 scopus 로고    scopus 로고
    • note
    • It is not clear yet why organocopper reagents prefer carbophilic attack to selenophilic attack.
  • 70
    • 0001729405 scopus 로고
    • Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford
    • For recent reviews, see: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: Oxford, 1991; Vol. 6, pp 461-484.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 461-484
    • Ogawa, A.1    Sonoda, N.2
  • 71
    • 0001611562 scopus 로고
    • Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Pergamon Press: Oxford
    • (b) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds; Pergamon Press: Oxford, 1995; Vol. 5, pp 231-255.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.5 , pp. 231-255
    • Ogawa, A.1    Sonoda, N.2
  • 74
    • 61849149973 scopus 로고    scopus 로고
    • note
    • As for the hitherto known synthetic methods of selenol esters, see the literature cited in ref 28b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.