The Effect of Pressure on Sigmatropic Rearrangements of Seven-Membered Conjugated Systems. [3,3] and [1,9] Sigmatropies
- 1 April 1989
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 62 (4) , 1143-1146
- https://doi.org/10.1246/bcsj.62.1143
Abstract
The kinetic features of the [1,9] sigmatropy (with 2-benzyloxy-3-bromotropone) and the [3,3] sigmatropy (with 2-allyloxytropone and 2-[(3-methyl-2-butenyl)oxy]tropone) were investigated under various pressures (1 to 1600 bar). The activation volume of [1,9] sigmatropy was of the same order as those of [1,5] sigmatropy of cyclopentadienes. The activation volume of [3,3] sigmatropy of more sterically-hindered substrate was more negative than that of the unhindered one.Keywords
This publication has 17 references indexed in Scilit:
- The Kinetic Evidence of the Concerted [1,9] Sigmatropy for the Acetyl Migration in the 2-Acetoxytropones. The NMR Spectral Analysis of the Seven-Fold Degenerated Acetotropy of HexaacetoxytroponeBulletin of the Chemical Society of Japan, 1987
- Effect of pressure on the rates of sigmatropic shifts. Volume as an indication of a wide mechanistic rangeJournal of the American Chemical Society, 1983
- Molecular design of tautomeric compoundsAccounts of Chemical Research, 1981
- Kinetics of reactions in solutions under pressure. 52. Effect of pressure on concerted and stepwise sigmatropic shiftsJournal of the American Chemical Society, 1978
- Thermal [1,j] sigmatropic rearrangementsChemical Reviews, 1976
- Solvent effects on the activation volume of a Diels-Alder reactionTransactions of the Faraday Society, 1970
- Organic Reactions under High Pressure. VI. Some Claisen and Cope RearrangementsJournal of the American Chemical Society, 1962
- The Volume Change of Activation in the Claisen and Curtius RearrangementsJournal of the American Chemical Society, 1961
- THE ENTHALPY-ENTROPY RELATIONSHIP AND ITS IMPLICATIONS FOR ORGANIC CHEMISTRYThe Journal of Organic Chemistry, 1955
- Claisen Rearrangement of 3-BromotropoloneProceedings of the Japan Academy, 1953