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The thermal transformations of bicyclopropylidene and methylenespiropentane revisited

Schill, H., Kozhushkov, S.I., Walsh, R. and de Meijere, A. (2007) The thermal transformations of bicyclopropylidene and methylenespiropentane revisited. European Journal of Organic Chemistry (9). pp. 1510-1516. ISSN 1434-193X

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To link to this item DOI: 10.1002/ejoc.200601100

Abstract/Summary

The overall and the individual rate constants of the unimolecular thermal isomerization of methylenespiropentane (4) to 1,2- and 1,3-dimethylenecyclobutanes (7 and 8) have been determined to be lg (k(-4)/s(-1)) = (13.78 +/- 0.06) - (49.7 +/- 0.2) kcal mol(-1)/RT.ln 10, lg(k(7)/s(-1)) = (13.03 +/- 0.19) - (48.0 +/- 0.6) kcal mol(-1)/RT.ln 10 and lg(k(8)/s(-1)) = (14.15 +/- 0.19) - (52.4 +/- 0.5) kcal mol(-1)/RT.ln 10, respectively. The activation energies are significantly lower than that for the rearrangement of the parent spiropentane. ((c) Wiley-VCH Verlag GmbH & Co.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11607
Uncontrolled Keywords:small ring systems, rearrangement, high-temperature chemistry, kinetics, strained molecules , UNIQUE TETRASUBSTITUTED ALKENE, VERSATILE C-6-BUILDING BLOCK, ORGANIC-SYNTHESIS, REARRANGEMENT, METHYLENECYCLOPROPANE, KINETICS, ISOMERIZATION, HYDROCARBONS, STRAIN, ALKYLIDENECYCLOPROPANES

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