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By M.P. CAVA and M.J. MITCHELL (Eds.)

ISBN-10: 0123957524

ISBN-13: 9780123957528

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CYCLOBUTADIENE 1. , tricyclooctadienes or products of their thermal rearrangement) under conditions which should be conducive to the generation of monomeric cyclobutadienes. The dimerization of a triplet cyclobutadiene species by cycloaddition is a process which undoubtedly is energetically favorable and leads to the formation of two new σ bonds without requiring spin inversion. Maximum overlap of π orbitals should be energetically favorable in the transition state of the dimerization (as it is in the Diels-Alder reaction), resulting in the formation of syn tricyclooctadienes (A).

In addition, tautomer (38) was transformed in several steps into a diketone (57) which was synthesized by an independent route. 1 50 No direct evidence regarding the configuration of dimers (35a) and (35b) is available as yet. f Subjecting dimethiodide (55) to Hofmann elimination in refluxing ter/-butyl * In this connection it is interesting to note that the sterically hindered analog of (29), l,l,4,4,5,5,8,8-octamethyl-l,2,3,4,5,6,7,8-octahydrobiphenylene, appears to undergo hydrogen abstraction and rearrangement reactions but not dimerization.

86 Interestingly enough, the preparation of difluoroacetylene has been claimed in two p a t e n t s 7 7' 1 13 and in one of these the isolation of a fluorocarbon, C 4 F 4 , possibly tetrafluorocyclobutadiene (58) was r e p o r t e d . ) on standing in the gaseous state at room temperature for several hours. 1 13 * When the dehalogenation of 1,2-dibromocyclohexene with sodium in ether was carried out in the presence of 1,3-diphenylisobenzofuran, an adduct of cyclohexyne was formed (Gwynn, 1962, ref.

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Cyclobutadiene and Related Compounds by M.P. CAVA and M.J. MITCHELL (Eds.)

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