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

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Additional resources for Cyclobutadiene and Related Compounds

Example text

CYCLOBUTADIENE When tetraphenylcyclobutadiene is generated by either of the above methods in the presence of oxygen (itself a triplet), c/s-dibenzoylstilbene (75) is formed, presumably by way of a four-membered peroxide intermediate (12). Similarly, when tetraphenylcyclobutadiene (11) is generated by thermolysis of the butadienyltin compound (70) in the presence of thiophenol (a good radical scavenger), a compound believed to be l-thiophenoxy-l,2,3,4-tetraphenylbutadiene (14) is formed, probably by way of the corresponding cyclobutene C 6H 5 C6H5 C 6H , C 6H 5 .

TRIPLET DIRADICAL CHARACTER 47 completely excluded at this time. However, such a structure would be expected to have less resonance stabilization than the triplet tetraphenylcyclobutadiene molecule. Butadiene (25) is formed in a number of pyrolytic reactions in which cyclobutadiene (22) would be expected to be generated. 02'5]deca-3,7,9-triene-7,8dicarboxylate ( 2 0 ) , 1 3' 18 and 2a,3,10,10a-tetrahydro-3,10-ethenocyclobuta[o]anthra-4,9-quinone (27) 1 3; and (c) the pyrolysis of l,3-bis(dimethylamino)cyclobutane dimethohydroxide (22).

T' 90 The dehalogenation of 3-methyl-1,2-dibromocyclohexene60 and the pyrolysis of silver 2-chlorocyclohexenecarboxylate82 also failed to afford such products. CH2- C=C-CH 2 / (CH2)M \:H 2- teC-CH2 (CH 2)„ + (CH^Tj (72) (71) (CH^J^ (73) ^JCH 2)„ (CH^Jjj (74) and/or CCH^l (75) (CH2)m ] ^ C H 2) „ (76) Attempts were made to prepare difluoroacetylene by several methods. 86 In the absence of any evidence to the contrary, it was reasonable to believe that difluoroacetylene might be made to undergo dimerization to give 1,2,3,4tetrafluorocyclobutadiene, which might be somewhat stabilized by the four electron-withdrawing fluorine atoms.

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