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Multiple thermal rearrangements. III. The pyrolysis of 7-(3-butenyl)-cycloheptatriene

✍ Scribed by C.A. Cupas; M.S. Kong; M. Mullins; W.E. Heyd

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
154 KB
Volume
12
Category
Article
ISSN
0040-4039

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✦ Synopsis

Nechanistic aspects of thermal sigmatropic rearrangements in cycloheptatrienes have been studied extensively.2 In contrast, the synthetic potential of these isomerization reactions has been exploited only recently. For example, a facile entry to tricyclo[4.3.1.03g8]decane (protoadamantane) derivatives is provided by the rearrangement of 7-allyloxycycloheptatriene (1).3

πŸ“œ SIMILAR VOLUMES

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Multiple thermal rearrangements. : IV. The pyrolysis of 2-(4-pentenyl)-dihydrotropone
✍ Leonard Hodakowski; Chris A. Cupas πŸ“‚ Article πŸ“… 1973 πŸ› Elsevier Science 🌐 French βš– 162 KB

In previous studies we have shown that the thermal rearrangement of appropriately substituded cycloheptatrienes and dihydrotropones provides a facile synthetic entry to new bridged polycyclic systems. For example, pyrolysis of 7-allyloxycycloheptatriene (lJ produces, in high yield, equal amounts of

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.