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Volumn , Issue 4, 2002, Pages 478-479

Mg-promoted stereoselective desulfonation of β-arylvinyl sulfone derivatives

Author keywords

[No Author keywords available]

Indexed keywords

MAGNESIUM; SULFONE DERIVATIVE; VINYL DERIVATIVE;

EID: 0036015364     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.478     Document Type: Article
Times cited : (10)

References (21)
  • 1
    • 0000871832 scopus 로고
    • ed. by B. M. Trost and I. Fleming, Pergamon, Oxford
    • "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 6, pp 949-1070.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 949-1070
  • 6
    • 0010529603 scopus 로고    scopus 로고
    • note
    • 6 for its (E) and (Z)-isomers were 7.66 and 7.27 ppm, respectively. Since some deshielding (0.6 ppm) can be elucidated by hydrogen bonding of the olefinic proton with an oxygen atom of the sulfonyl group, 2a was identified as the (E)-isomer. An olefinic proton of the other isomer came out at δ = 7.18 ppm.
  • 9
    • 0010529604 scopus 로고    scopus 로고
    • note
    • Mg turnings for Grignard reaction was used without any pre-treatment.
  • 10
    • 0010598486 scopus 로고    scopus 로고
    • note
    • The reaction of 2a in DMSO was found to give the optimum yield (68%) among those in other aprotic polar solvents such as DMF (45%), sulforane (40%), DMAC (23%), THF (20%), and acetonitrile (14%).
  • 11
    • 0010598487 scopus 로고    scopus 로고
    • note
    • Although the detailed role of TMSCl is still unclear, two main roles may be postulated, i.e., activation of the surface of Mg metal and stabilization of anionic intermediates generated by electron transfer from Mg metal.
  • 12
    • 0010563631 scopus 로고    scopus 로고
    • note
    • Mg metal is thought to be able to reduce readily compounds possessing less negative reduction potential than -1.80 V vs Ag/AgCl under these conditions. See Ref. 11.
  • 19
    • 0010529605 scopus 로고    scopus 로고
    • note
    • 5MgBr led to stereospecific reductive desulfination to give (Z)-β-(methylthio)styrene in a 79% yield.
  • 21
    • 0010561964 scopus 로고    scopus 로고
    • note
    • 2O after the reaction in DMSO resulted in no formation of 3a-D to give 3a-H as the sole product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.