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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 22
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Original Articles

Synthesis of 1‐Aryl‐1,2,3,4,5,6‐hexahydrophosphinine 1‐Oxides

, , , , , & show all
Pages 4159-4169 | Received 30 Mar 2004, Published online: 10 Jan 2011
 

Abstract

Possibilities for the synthesis of 1‐(2,4,6‐triisopropylphenyl‐)1,2,3,4,5,6‐hexahydrophosphinine oxide (2) have been explored. The trivial method based on the hydrogenation of the corresponding dihydrophosphinine oxides (8a–e) was suitable only for the preparation of hexahydrophosphinine oxides containing a trimethylphenyl or methylphenyl group on the phosphorus atom (9a–c). The triisopropylphenyl product (2) was synthesized by the stepwise reduction of the double bonds of starting material 1. Hence, the ring contraction side reaction, observed during the catalytic hydrogenation, could be eliminated. The unusual reactivity was studied by quantum chemical calculations.

Acknowledgments

The authors are grateful for the OTKA support of the work (Grant No. T 042479). The advice of Professor Emeritus Dr Harry R. Hudson (London Metropolitan University) is appreciated.

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