Synthesis and Electrophilic Cyclization Reactions of Diphenyl 3-Methylpenta-1,2,4-trienyl Phosphine Oxide

Abstract

Diphenyl 3-methyl-penta-1,2,4-trienyl phosphine oxide can be readily prepared via an atom-economical [2,3]-sigmatropic rearrangement of the mediated alkenynyl phosphinite formed in situ by reaction of 3-methylpent-1-en-4-yn-3-ol with diphenylchlorophosphine. Electrophilic cyclization reactions of the vinylallenyl phosphine oxide prepared were investigated as it was established that the reactions proceeded with formation of various heterocyclic or highly unsaturated compounds with participation of the allenic and/or 1,3-dienic part of the vinylallenic system with neighboring group participation of phosphoryl and/or vinylic group.

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GRAPHICAL ABSTRACT

Keywords:

• 2,5-Dihydro-1,2-oxaphosphole
• electrophilic cyclization
• neighboring group participation
• selenophene
• thiophene
• 3-vinylallenyl phosphine oxide

ACKNOWLEDGMENTS

Support from the Research Fund of the Konstantin Preslavsky University of Shumen (Projects No. RD-05-367 / 2010 and No. RD-05-137 / 2011) is acknowledged. Special thanks to Hasan Hasanov for the technical help in the chromatographical separations.

Notes

Dedicated to Professor Dr. Toru Minami from Kyushu Institute of Technology, Kitakyushu, Japan, on the occasion of his 70th birthday.