高价碘（III）试剂作为α-硝基-α-重氮羰基化合物的安全替代品。

Hypervalent iodine(III) reagents as safe alternatives to alpha-nitro-alpha-diazocarbonyls.

作者信息

Wurz Ryan P, Charette André B

机构信息

Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.

出版信息

Org Lett. 2003 Jun 26;5(13):2327-9. doi: 10.1021/ol034672g.

DOI:10.1021/ol034672g

PMID:12816440

Abstract

A cyclopropanation reaction involving iodonium ylides generated in situ allows for efficient preparation of substituted 1-nitro-1-carbonyl cyclopropanes. This robust cyclopropanation reaction can be performed in organic solvents, biphasic aqueous media, or under solvent-free conditions with alkene substrates. The iodonium ylides generated in situ display some surprising differences in reactivity when compared to alpha-nitro-alpha-diazocarbonyl compounds. They do not undergo O-H insertion reactions and exhibit reduced reactivity with certain alkenes. [reaction: see text]

摘要

涉及原位生成的碘鎓叶立德的环丙烷化反应能够高效制备取代的1-硝基-1-羰基环丙烷。这种稳健的环丙烷化反应可以在有机溶剂、双相水性介质中进行，或者在无溶剂条件下与烯烃底物反应。与α-硝基-α-重氮羰基化合物相比，原位生成的碘鎓叶立德在反应性上表现出一些惊人的差异。它们不会发生O-H插入反应，并且与某些烯烃的反应性降低。[反应：见正文]