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 34 条

[1]

BARBARELLA G, 1989, J MOL STRUCT THEOCHE, V186, P197

[2]

BIELLMANN JF, 1968, B SOC CHIM FR, P1154

[3]

BIELLMANN JF, 1966, TETRAHEDRON LETT, V7, P3991

[4] SULFOXYLATE ION (HSO2-), THE HYDRIDE DONOR IN DITHIONITE-DEPENDENT REDUCTION OF NAD+ ANALOGS [J].