7360-96-5Relevant academic research and scientific papers
Thermal valence isomerization of cis-fused bicyclic cyclobutenes. A study of orbital symmetry control
Dauben, William G.,Michno, Drake M.
, p. 2284 - 2292 (2007/10/19)
This study shows that thermally promoted valence isomerizations of cis-fused bicyclic cyclobutenes, when free of steric constraint, yield products arising from both orbital symmetry allowed conrotatory openings of the labile σ bond in the cyclobutene ring. In the case of the related vinylcyclobutenes, one conrotatory mode produces a stable cis,trans,cis monocyclic triene whereas fission in the other allowed sense affords a thermally labile trans,cis,cis monocyclic triene which, in turn, cyclizes to yield a cyclohexadiene derivative. The product distributions are evaluated in terms of secondary orbital interactions.
Thermal Isomerisation of Cyclic cis, trans, cis-Trienes
Dauben, William G.,Michno, Drake M.,Olsen, Eric G.
, p. 687 - 690 (2007/10/02)
The thermal isomerisation of a series of cyclic conjugated cis, trans, cis-trienes was examined.The results obtained show a structure-reactivity correlation between the size of the ring vs. the type of product observed.The eleven-membered-ring triene (4) yields a novel tricyclic isomer 8, whereas the nine-membered-ring triene (5) yields the bicyclic diene 9.The ten-membered analogue 3 yields a mixture of both types of observed products.Mechanistic possibilities are proposed to explain the formation of both types of products.
