The gas phase thermal chemistry of several halocyclopropenes has been investigated. In each instance the cyclopropene was converted cleanly to an allene.
Regioselective Allene Synthesis and Propargylations with Propargyl Diethanolamine Boronates
作者:Daniel R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake
DOI:10.1021/ol9022529
日期:2009.12.3
The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.