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The chemistry of cycloheptatriene: Part VIII: Transannular 1-5 shifts of hydrogen in phenylcycloheptatriene

✍ Scribed by A. P. ter Borg; H. Kloosterziel

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
714 KB
Volume
82
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

7‐Phenylcycloheptatriene‐1,3,5 rearranges on heating to a mixture of the 3‐, 1‐ and 2‐isomers. These are formed in the order indicated by successive trans‐annular 1‐5 shifts of hydrogen. The isomerization of the 7‐ to the 3‐isomer, by which the trienic and aromatic systems enter into conjugation, is appreciably faster than the 1‐5 shift in cycloheptatriene itself. The interconversion of the 3‐ and 1‐isomers, however, proceeds at a rate comparable with that of the unsubstituted compound.

The nature of the solvent has no influence on the rate of the 1‐5 shift.

πŸ“œ SIMILAR VOLUMES

The chemistry of cycloheptatriene: Part
The chemistry of cycloheptatriene: Part IX: Thermal interconversion of 2,7- and 2,3-dihydrotropone by transannular 1-5 shifts of hydrogen
✍ A. P. ter Borg; H. Kloosterziel πŸ“‚ Article πŸ“… 2010 πŸ› Elsevier Science 🌐 English βš– 352 KB

## Abstract 2,7‐Dihydrotropone upon heating at 60‐100deg; isomerizes (partly) to the 2,3‐isomer. Kinetic data: order of the reaction, influence of solvent and entropy of activation, point to a mechanism involving an intramolecular 1‐5 shift of hydrogen in this cycloheptadiene derivative.