Experimental and theoretical studies on the conjugation of the phosphorus-carbon double bond with a cyclopropyl group

Shigeo Kimura; Shigekazu Ito; Masaaki Yoshifuji; Tamás Veszprémi

doi:10.1021/jo034648g

Experimental and theoretical studies on the conjugation of the phosphorus-carbon double bond with a cyclopropyl group

J Org Chem. 2003 Aug 22;68(17):6820-3. doi: 10.1021/jo034648g.

Authors

Shigeo Kimura¹, Shigekazu Ito, Masaaki Yoshifuji, Tamás Veszprémi

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Aoba, Sendai 980-8578, Japan.

PMID: 12919058
DOI: 10.1021/jo034648g

Abstract

X-ray structural analysis for (Z)-2-cyclopropyl-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaethene (2) was performed to confirm that the cyclopropyl group largely interacts with the P[double bond]C group compared with its carbon analogue, vinylcyclopropane (1). Absorption spectrum and redox properties of 2 were also studied to prove the conjugation. Theoretical investigation for nonsubstituted derivatives (4) indicated conjugative interaction between the P[double bond]C and cyclopropyl groups and revealed the physicochemical similarities between the P=C and C[double bond]C.