Migration of an acyl group in glycerol derivatives: II. Transformation of diacylglycerol-β-iodohydrins into diphenyl diacylglycerol-α-phosphates
✍ Scribed by M. A. Hoefnagel; Mrs. A. H. Hartman-Köhler; P. E. Verkade
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 828 KB
- Volume
- 80
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
The action of silver diphenyl phosphate on a diacylglycerol‐α‐iodohydrin or the isomeric diacylglycerol‐β‐iodohydrin in benzene as medium gives the diphenyl diacylglycerol‐α‐phosphate in practically equal and very satisfactory yields. In the latter case therefore a migration of an acyl group from an α‐ into the β‐position occurs.
The reaction has been studied for the compounds with stearoyl, 4‐methoxybenzoyl, and 2,6‐dimethyl‐4‐nitrobenzoyl as the acyl group. It proceeds almost equally smoothly in all cases.
On the basis of these facts the reaction mechanism is briefly discussed.