Efficient photochemical synthesis of 2-vinylcyclopropanecarbaldehydes, precursors of cyclopropane components present in pyrethroids, by using the oxa-di-π-methane rearrangement
作者:Diego Armesto、Maria J. Ortiz、Antonia R. Agarrabeitia、Noureddin El-Boulifi
DOI:10.1016/j.tet.2010.09.012
日期:2010.11
oxa-di-π-methane rearrangement (ODPM) to afford the corresponding cyclopropanecarbaldehydes 16a–f and 17 in yields ranging from 14% to 62% in addition in most cases to products resulting from decarbonylation. However, when 4-phenylbenzophenone is used as the photosensitizer ODPM products are obtained exclusively in almost quantitative yield. These are additional examples of the recently described, unexpected influence
以3-甲氧基苯乙酮和4-苯基二苯甲酮为敏化剂,对一系列β,γ,δ,γ-不饱和醛14a - f和15的三重态光反应性进行了比较研究。当将3-甲氧基苯乙酮用作三重态敏化剂时,醛进行氧杂二-二-甲烷重排(ODPM),得到相应的环丙烷甲醛16a – f和17在大多数情况下,除脱羰作用产生的产品外,其收率范围为14%至62%。然而,当使用4-苯基二苯甲酮作为光敏剂时,仅以几乎定量的产率获得了ODPM产物。这些是最近描述的三重态敏化剂的性质对有机化合物的光反应性的意外影响的其他实例。