✦ LIBER ✦
Phosphonic systems. Part 15. Addition of diethyl prop-2-enylphosphonate to aldehydes: Fragmentation vs. isomerization of kinetic products
✍ Scribed by Elmar L. Muller; Tomasz A. Modro
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 470 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1042-7163
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Lithiated diethyl prop‐2‐enylphosphonate adds to an aliphatic or an aromatic aldehyde, yielding a diastereomeric mixture of the kinetically controlled α‐adduct. Upon warming, these adducts decompose back to starting materials to give finally the thermodynamically controlled γ‐adducts, or undergo fragmentation to diethyl phosphate and (E) dienes. The distribution of the first product between these two pathways is a function of the aldehyde (aromatic vs. aliphatic) and of steric interactions operating within the two diastereomers of the adduct.