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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Isomers
NAD
Carbon
dihydronicotinamide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Steric acceleration of reductive desulfonation of 1,8-naphthalenedisulfonate by an NADH model compound. / Shinkai, Seiji; Kuroda, Hideo; Kusano, Yumiko; Manabe, Osamu; Ito, Akiyoshi.

In: Tetrahedron Letters, Vol. 22, No. 33, 01.01.1981, p. 3201-3204.

Research output: Contribution to journalArticle

Shinkai, Seiji ; Kuroda, Hideo ; Kusano, Yumiko ; Manabe, Osamu ; Ito, Akiyoshi. / Steric acceleration of reductive desulfonation of 1,8-naphthalenedisulfonate by an NADH model compound. In: Tetrahedron Letters. 1981 ; Vol. 22, No. 33. pp. 3201-3204.
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