The deoxy-conduritol (lct,2ot,4l~)-l,2,4-trihydroxycyclohex-5-ene (6) has been prepared in racemic form from 1,4-benzoquinone in a six-step sequence, the key reaction involving a monohalide displacement by anchimeric assistance in the diacetoxy-dibromo compound previously employed for a synthesis of
Anchimeric assistance in the gas phase dehydrohalogenation of 5-chloro-2-methylpent-2-ene
✍ Scribed by Gabriel Chuchani; Ignacio Martin; Miguel E. Alonso; Patricia Jano
- Book ID
- 102447527
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- English
- Weight
- 268 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0538-8066
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
5‐Chloro‐2‐methylpent‐2‐ene decomposes at temperatures of 370–420°C with initial pressures from 61to 158 torr to yield hydrogen chloride and a mixture of methylpentadiene isomers. In a static system, with seasoned vessel and propene inhibitor, the reaction is homogeneous, unimolecular, and of the first order. The rate coefficient is expressed by the following Arrhenius equation: log k (sec^−1^) = (13.43 ± 0.30) − (215.0 ± 3.7) kJ/mol/2.303__RT__. The result ofthe present work additionally supports the participation of the neighboringaliphatic olefinic double bond in the rate of HCl elimination of alkenyl chlorides in the gas phase. Moreover, it also confirms the three‐membered conformation as the most favored structure for anchimeric assistance.
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