Diverse Annulations of Alkyl(phenyl)phosphinic Chlorides and Imines.

Org Lett

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.

Published: January 2025

The reactivity of alkyl(aryl)phosphinic chlorides and imines was investigated in the presence of a base. The results indicated that allyl/benzyl(aryl)phosphinic chlorides gave rise to 1,2-azaphosphines (δ-phostims), while nonbenzylic alkyl(aryl)phosphinic chlorides produced the corresponding β-phosphinolactams (β-phostims) in their reaction with cyclic dibenzo[,][1,4]oxazepines, whereas steric electron-rich arylmethyl(aryl)phosphinic chlorides generated [2 + 2 + 2] annuloadducts in some cases. The current investigation provides useful insight into the reactivity of phosphinic chlorides and imines.

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http://dx.doi.org/10.1021/acs.orglett.4c04737DOI Listing

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