Steric acceleration of reductive desulfonation of 1,8-naphthalenedisulfonate by an NADH model compound

Seiji Shinkai, Hideo Kuroda, Yumiko Kusano, Osamu Manabe, Akiyoshi Ito

Research output: Contribution to journalArticle

Abstract

1,8-Naphthalenedisulfonate was reductively desulfonated by N-benzyl-1,4-dihydronicotinamide, whereas no desulfonation was observed for the 1,6-isomer. The high reactivity of the 1,8-isomer is attributed to the steric-strain that enforces the shift of the initial state with the sp2 -carbon close to the transition state with the sp3 - carbon.

Original languageEnglish
Pages (from-to)3201-3204
Number of pages4
JournalTetrahedron Letters
Volume22
Issue number33
DOIs
Publication statusPublished - Jan 1 1981
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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