Issue 5, 1973

A stereochemical study of some reactions of compounds in the 4-methyl-1,3,2-dioxaphosph(V)orinan series

Abstract

Stereochemistries are assigned to the geometrical isomers of the secondary phosphite 4-methyl-2-oxo-1,3,2-dioxaphosphorinan (I) on the basis of n.m.r. and dipole moment measurements. Chlorination of the isomers of (I) leads stereospecifically to isomers of the chloridate (III). Both isomers of (III) react stereospecifically with piperidine to yield the corresponding piperidide. The cis-form undergoes methanolysis with high stereospecificity whereas the trans-form is methanolysed with low stereospecificity. The stereochemistries of some reactions of the chloridite 2-chloro-4-methyl-1,3,2-dioxaphosphorinan (II) and the phosphite 2-methoxy-4-methyl-1,3,2-dioxaphosphorinan are also described. The interconversion and relative stabilities of the isomers of (I) have been examined.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1973, 676-681

A stereochemical study of some reactions of compounds in the 4-methyl-1,3,2-dioxaphosph(V)orinan series

C. L. Bodkin and P. Simpson, J. Chem. Soc., Perkin Trans. 2, 1973, 676 DOI: 10.1039/P29730000676

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements