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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:

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

DOI: 10.1021/acs.joc.7b00346

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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.

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alkyne synthesis developed in this study

Key Words

internal alkynes, terminal alkynes

ID: J42-Y2017