INTRAMOLECULAR ADDITION-REACTIONS OF CARBONYL YLIDES FORMED DURING PHOTOCYCLIZATION OF ARYL VINYL ETHERS

被引：11

作者：

DITTAMI, JP ^{[1
]}

NIE, XY ^{[1
]}

NIE, H ^{[1
]}

RAMANATHAN, H ^{[1
]}

BREINING, S ^{[1
]}

BORDNER, J ^{[1
]}

DECOSTA, DL ^{[1
]}

KIPLINGER, J ^{[1
]}

REICHE, P ^{[1
]}

WARE, R ^{[1
]}

机构：

[1] PFIZER INC,CENT RES,GROTON,CT 06340

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 19期

关键词：

D O I：

10.1021/jo00019a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

引用

页码：5572 / 5578

页数：7

共 31 条

[1] PHOTOADDITION OF NAPHTHALENE AND ACRYLONITRILE - X-RAY AND NUCLEAR MAGNETIC-RESONANCE STUDY OF CYCLOADDUCTS [J].