PHOTOCHEMICAL DECOMPOSITION OF 1-ALKOXY-2-AZIDOPHENAZINES - ADDITION OF NITRENES TO AZIDES

被引：2

作者：

ALBINI, A ^{[1
]}

BETTINETTI, G ^{[1
]}

MINOLI, G ^{[1
]}

机构：

[1] UNIV PAVIA,DEPT AGR SCI & RURAL DEV,I-27100 PAVIA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 25期

关键词：

D O I：

10.1021/jo00025a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photolysis of 2-azido-1-methoxyphenazine (1a) and its ethoxy homologue (1b) takes an unusual course. It involves the addition of a singlet nitrene or one of its cyclic tautomers to the ground-state azide to form the N-phenazinyl iminoether 9a (from 1a) and a 2-oxazolo[5,4-a]phenazinyl derivative of a quinoxalinylpropenenitrile (10, from both 1a and 1b). Products derived from the triplet nitrene are formed as well. The effects of varying some of the experimental conditions were determined. A mechanism for the photolysis is proposed.

引用

页码：6993 / 6997

页数：5

共 19 条

[1] PREPARATION + PROPERTIES OF IMIDO INTERMEDIATES ( IMIDOGENS ) [J].

ABRAMOVITCH, RA ;

DAVIS, BA .

CHEMICAL REVIEWS, 1964, 64 (02) :149-&

[2]

ABRAMOVITCH RA, 1971, CHEM AZIDO GROUP, P256

[3] INTERMOLECULAR AND INTRAMOLECULAR REACTIONS OF NITRENES AND THEIR CYCLIC ISOMERS IN THE PHOTODECOMPOSITION OF SOME SUBSTITUTED 2-AZIDOPHENAZINES [J].

ALBINI, A ;

BETTINETTI, G ;

MINOLI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1245-1251

[4]

ALBINI A, 1982, GAZZ CHIM ITAL, V112, P15

[5]

BETTINETTI GF, 1979, GAZZ CHIM ITAL, V109, P175

[6]

BETTINETTI GF, 1980, GAZZ CHIM ITAL, V110, P135

[7]

CROW WD, 1968, TETRAHEDRON LETT, P6149

[8] PHOTOLYTIC RING-EXPANSIONS OF 6-AZIDOQUINOLINES AND 6-AZIDODIAZINES - SOME UNEXPECTED AZEPINE RING-OPENING REACTIONS [J].

HAYES, R ;

SCHOFIELD, JM ;

SMALLEY, RK ;

SCOPES, DIC .

TETRAHEDRON, 1990, 46 (06) :2089-2096

[9] DEVELOPMENTS IN ARYLNITRENE CHEMISTRY - SYNTHESES AND MECHANISMS [J].

IDDON, B ;

METHCOHN, O ;

SCRIVEN, EFV ;

SUSCHITZKY, H ;

GALLAGHER, PT .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (12) :900-917

[10]

KITSON RE, 1952, ANAL CHEM, V24, P335

← 1 2 →