An Efficient Flow-Photochemical Synthesis of 5H-Furanones Leads to an Understanding of Torquoselectivity in Cyclobutenone Rearrangements

被引：44

作者：

Harrowven, David C. ^{[1
]}

Mohamed, Mubina ^{[1
]}

Goncalves, Theo P. ^{[1
]}

Whitby, Richard J. ^{[1
]}

Bolien, David ^{[1
]}

Sneddon, Helen F. ^{[2
]}

机构：

[1] Univ Southampton, Southampton SO17 1BJ, Hants, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 18期

基金：

英国工程与自然科学研究理事会;

关键词：

cyclobutenones; density functional calculations; photochemistry; rearrangements; small ring systems; ELECTROCYCLIC REACTIONS; ACID; HYDROXYQUINONES; ROUTE; BOND;

D O I：

10.1002/anie.201200281

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Go with the flow: 4-Hydroxycyclobutenones were efficiently transformed into 5H-furanones using an inexpensive flow-photochemical setup. The results challenge the notion that this and the related thermochemical rearrangement display torquoselectivity in their electrocyclic opening to a vinylketene intermediate. Selectivity in the photochemical rearrangement is due a dichotomous reactivity of the (E)- and (Z)-vinylketene intermediates (see scheme). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：4405 / 4408

页数：4

共 29 条

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