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Synthesis 1998; 1998(2): 125-138
DOI: 10.1055/s-1998-2007
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The Ene Reaction in the Chemistry of Low-Coordinate Phosphorus

Thomas W. Mackewitz* , Manfred Regitz
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67663 Kaiserslautern, Germany; Fax + 49(6 31)2 05 39 21; E-mail: regitz@rhrk.uni.kl.de
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Publication Date:
31 December 2000 (online)

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The ene reaction belongs to one of the simplest and most versatile reaction categories in organic chemistry. Recently ene reactions involving compounds of low-coordinate phosphorus, phospha-ene reactions, have found wide application in the synthesis of different classes of organophosphorus compounds. For phospha-ene reactions, four main types are currently known which involve the employment of phosphaalkenes, iminophosphines and phosphaalkynes. Also included are retro-phospha-ene reactions, which reveal access to short-lived and highly reactive phosphaalkenes. The experimentally observed regiochemistry is in agreement with MO calculations, carried out on the simplest parent reactions of type I - IV.

phospha-ene reactions - phosphaalkenes - iminophosphines - phosphaalkynes - tandem ene reactions - ab initio calculations

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