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

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

doi:10.1016/S0040-4039(01)81863-3

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 journal › Article › peer-review

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 language	English
Pages (from-to)	3201-3204
Number of pages	4
Journal	Tetrahedron Letters
Volume	22
Issue number	33
DOIs	https://doi.org/10.1016/S0040-4039(01)81863-3
Publication status	Published - 1981
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)81863-3

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

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.",

author = "Seiji Shinkai and Hideo Kuroda and Yumiko Kusano and Osamu Manabe and Akiyoshi Ito",

year = "1981",

doi = "10.1016/S0040-4039(01)81863-3",

language = "English",

volume = "22",

pages = "3201--3204",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "33",

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TY - JOUR

T1 - Steric acceleration of reductive desulfonation of 1,8-naphthalenedisulfonate by an NADH model compound

AU - Shinkai, Seiji

AU - Kuroda, Hideo

AU - Kusano, Yumiko

AU - Manabe, Osamu

AU - Ito, Akiyoshi

PY - 1981

Y1 - 1981

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=49149135305&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=49149135305&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(01)81863-3

DO - 10.1016/S0040-4039(01)81863-3

M3 - Article

AN - SCOPUS:49149135305

SN - 0040-4039

VL - 22

SP - 3201

EP - 3204

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 33

ER -

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

Abstract

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