Strained hydrocarbons from cyclic diynes-preparation and reactivity

The reaction of cyclic diynes with either CpCo(CO)2 or AlCl3 yielded strained hydrocarbons in which a Dewar benzene or a tricyclo[4.2.0.02,5]octa‐3,7‐diene frame is bridged by hydrocarbon chains. The photochemistry and thermochemistry of these species are discussed. Results of quantum chemical calcu...

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Published in:Journal of physical organic chemistry 2002-08, Vol.15 (8), p.484-489
Main Authors: Bethke, Sabine, Brand, Stefan, Treptow, Björn, Gleiter, Rolf
Format: Article
Language:English
Subjects:
alkynes
cage compounds
DFT calculations
photochemistry
strained hydrocarbons
thermal rearrangements
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description The reaction of cyclic diynes with either CpCo(CO)2 or AlCl3 yielded strained hydrocarbons in which a Dewar benzene or a tricyclo[4.2.0.02,5]octa‐3,7‐diene frame is bridged by hydrocarbon chains. The photochemistry and thermochemistry of these species are discussed. Results of quantum chemical calculations (DFT, CASPT2) are used to discuss the thermochemistry of four different fourfold bridged tricyclo[4.2.0.02,5]octa‐3,7‐dienes. Depending on the bridging mode, either a Cope‐type rearrangement or a ring opening reaction is preferred. Copyright © 2002 John Wiley & Sons, Ltd.
doi_str_mv 10.1002/poc.500
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subjects alkynes
cage compounds
DFT calculations
photochemistry
strained hydrocarbons
thermal rearrangements
title Strained hydrocarbons from cyclic diynes-preparation and reactivity
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