Bicyclo[2,2,1]heptylphosphonates II. Stéréochimie de l'addition de Diels–Alder du vinylphosphonate de diméthyle sur quelques cyclopentadiènes; étude par r.m.n.

Abstract

The stereochemistry of the Diels–Alder addition of the vinylphosphonate (1) to cyclopentadiene, hexachlorocyclopentadiene (6), dimethoxytetrachlorocyclopentadiene (8), and pentachlorocyclopentadiene (10) has been studied. The configuration of the compounds has been proved by chemical correlation and essentially by n.m.r. spectroscopy. The study of the n.m.r. spectra confirms the 31P,1H vicinal coupling dihedral angular dependence and suggests an electronegativity range for the —P(O)(OCH3)2 group.