Organic Chemistry Portal

Abstracts

Search:

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Hiroki Yoneyama, Masahiro Numata, Kenji Uemura, Yoshihide Usami and Shinya Harusawa*

*Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan, Email: harusawagly.oups.ac.jp

H. Yoneyama, M. Numata, K. Uemura, Y. Usami, S. Harusawa, J. Org. Chem., 2017, 82, 5538-5556.

DOI: 10.1021/acs.joc.7b00346


see article for more reactions

Abstract

Cyanophosphates (CPs) can be easily prepared from carbonyl compounds, and their reaction with azides provides tetrazoles. A successive termal fragmentation of the tetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous internal and terminal alkynes in good yields under neutral conditions.

see article for more examples

alkyne synthesis developed in this study



Key Words

internal alkynes, terminal alkynes


ID: J42-Y2017