Intrinsic migration aptitudes of alkyl groups in a pinacol rearrangement
✍ Scribed by Eckehardt Wistuba; Christoph Rüchardt
- Book ID
- 104234399
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 201 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
## swnmary: Completely stereospecific 1,2-migration of alkyl groups was achieved in Et2AlCL- prowted pinacoZ-type rearrangement of chiral B-mesyZoxy alcohols to give optically pure aalkyl ketones including both enantiomers of 4-methyl-3-hexanone, an alarm pheromone of ant.
## Abstract The migratory aptitude of the ethoxycarbonyl group in the pinacol rearrangement was deduced from the structure of the products observed after treatment of 2‐substituted 2,3‐dihydroxy‐3‐phenylbutyrates with fluorosulfonic acid at 0° for 3 minutes. The migratory aptitude of ethoxycarbonyl
DFT calculations at the Becke3LYP/6-31G\* level were employed to demonstrate that the pinacol rearrangement of ethylene glycol and the 1,1-dimethyl and 1,1,2-trimethyl analogs undergo pinacol rearrangements by a concerted hydrogen-bridged transition structure. No evidence for a bridged intermediate