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Synthesis 1995; 1995(4): 361-369
DOI: 10.1055/s-1995-3935
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2-Substituted Cycloiminium Salts in Azaphosphole Synthesis

Raj K. Bansal1 , Konstantin Karaghiosoff2 , Neelam Gandhi1 , Alfred Schmidpeter2
  • 1Department of Chemistry, University of Rajasthan, Jaipur 302004, India
  • 2Institut für Anorganische Chemie der Universität München, Meiserstr. 1, D-80333 München, Germany, FAX +49(89)5902578; E-mail ui161aa@sunmail.lrz-muenchen.de
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Publication Date:
31 December 2000 (online)

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The [4+1] cyclocondensation reaction of 2-alkyl- and 2-aminocycloiminium salts with suitable phosphorus(III) reagents provides an easy access to a large variety of anellated azaphospholes with a bridgehead nitrogen atom. This [4+1] approach is complemented by two related synthetic routes which, in place of the 2-substituted cycloiminium salts, use 2-unsubstituted 1-alkylcycloiminium salts or neutral 2-amino-substituted cyclic imines, and which thus follow the [3+2] pattern. In these cases, the ring is formed by cycloaddition with phosphaalkynes or by cyclocondensation with chloromethyldichlorophosphane, respectively.

cycloiminium salts - cyclocondensation - cycloaddition - anellated azaphospholes - dichlorophosphino derivatives