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Volumn , Issue 13, 2008, Pages 2023-2032

Development of a tandem base-catalyzed, triphenylphosphine-mediated disulfide reduction-Michael addition

Author keywords

Benzothiazepinones; Michael additions; Reductions; Thiols; Triphenylphosphine

Indexed keywords

ORGANIC COMPOUNDS; REDUCING AGENTS;

EID: 47349086967     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067102     Document Type: Article
Times cited : (29)

References (74)
  • 60
    • 47349113623 scopus 로고    scopus 로고
    • The 1H NMR spectra of the isolated products confirmed the presence of a free hydroxy group as we would expect for compounds derived by thiol addition. The thiol moiety of 4-sulfanylphenol is the strongest and the most-reactive nucleophile in the compound as it has a pKa of 6.8 compared with the hydroxy group pKa of 12.4. However, the phenol is still a reactive species that could possibly undergo Michael addition under basic conditions if the disulfide reduction was too slow and the more-reactive thiol was not formed quickly enough. To confirm that the disulfide reduction occurred first in our protocol and that side products derived from a phenol addition were not formed, we repeated the experiment reported in entry 1 of Table 1 without adding triphenylphosphine. In this case, phenol addition was not observed, even after heating the reaction overnight
    • a of 12.4. However, the phenol is still a reactive species that could possibly undergo Michael addition under basic conditions if the disulfide reduction was too slow and the more-reactive thiol was not formed quickly enough. To confirm that the disulfide reduction occurred first in our protocol and that side products derived from a phenol addition were not formed, we repeated the experiment reported in entry 1 of Table 1 without adding triphenylphosphine. In this case, phenol addition was not observed, even after heating the reaction overnight.
  • 74
    • 47349095455 scopus 로고    scopus 로고
    • 1H NMR spectra in accordance with data reported in the Wiley Subscription Services Inc., USA.
    • 1H NMR spectra in accordance with data reported in the Wiley Subscription Services Inc., USA.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.