On the structure of intermediate adducts arising from dithionite reduction of pyridinium salts: a novel class of derivatives of the parent sulfinic acid

被引：21

作者：

Carelli, V

Liberatore, F

Scipione, L

Musio, R

Sciacovelli, O

机构：

[1] Univ Rome La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biologi, I-00185 Rome, Italy

[2] Univ Bari, Dipartmento Chim, CNR, Ctr Studi Metodol Innovat Sintesi Organ, I-70126 Bari, Italy

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 08期

关键词：

pyridinium salts; dithionite reduction; parent sulfinic acid derivatives; C-13 and O-17 NMR spectroscopy;

D O I：

10.1016/S0040-4039(99)02251-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

C-13 and O-17 NMR spectroscopy show that adducts arising from dithionite reduction of 3- or 3,5-cyano- or carbamoyl-substituted pyridinium salts to the corresponding 1,4-dihydropyridines, are S-anions of esters of the simplest parent sulfinic acid. A pathway for formation of the 1,4-dihydropyridines, involving an intramolecular hydride transfer, is suggested. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1235 / 1240

页数：6

共 3 条

[1] STRUCTURE OF INTERMEDIATE IN SODIUM DITHIONITE REDUCTION OF PYRIDINIUM SALTS
BIELLMANN, JF
CALLOT, HJ
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1969, (04): : 1299 - +
[2] STRUCTURE AND REACTIVITY OF INTERMEDIATE FORMED IN SODIUM DITHIONITE REDUCTION OF PYRIDINIUM SALTS
BIELLMANN, JF
CALLOT, HJ
BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1968, (03): : 1154 - +
[3] Structure of the dimers arising from one-electron electrochemical reduction of pyridinium salts 3,5-disubstituted with electron-withdrawing groups
Carelli, V
Liberatore, F
Tortorella, S
Di Rienzo, B
Scipione, L
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (04): : 542 - 547

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