Studies on Intramolecular Cyclization of 2,4,6-Tri-Tert-Butylphenyl–P=C:In Memory of Professor Dr. Friedrich Bickelhaupt, Scheikundig Laboratorium, Vrije Universiteit, Amsterdam

GRAPHICAL ABSTRACT

Abstract

The intramolecular C–H insertion of the Mes*-substituted phosphanylidenecarbene [Mes*P=C:] (Mes* = 2,4,6-t-Bu₃C₆H₂) and characters of the cyclization product, 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene, were studied based on ab initio and density functional theory calculations.

Keywords:

• Intramolecular cyclization
• phosphanylidenecarbene
• 2,4,6-tri-tert-butylphenyl
• C‒H insertion
• Fritsch–Buttenberg–Wiechell reaction
• theoretical calculation

ACKNOWLEDGMENTS

One of the authors (Masaaki Yoshifuji) thanks Prof. A. J. Arduengo, III, The University of Alabama, for supporting the work on phosphanylidenecarbene and the related species described in this article.