By M.P. CAVA and M.J. MITCHELL (Eds.)
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However, all attempts to dehydrohalogenate the dibromide to l-bromo-2-dimethylamino-3-nitro-4-phenylcyclobutadiene (37) led only to uncharacterizable amorphous products. 30 30 1. Cl C 6H 5 2 N Y^F NR2 (31) (30) (29) ° 0 2N 0 2N - Η (32): R = ( C H 3) , C 2H 5, C 4H 9, or R 2 = ( C H 2) 4 (33) One of the stereoisomers (41a) of l,3-dinitro-2,4-diphenyl-3-bromocyclobutene (prepared from a β-nitrostyrene photodimer) gave only the ringcleavage product, l,3-dinitro-2,4-diphenyl-l-bromo-l,4-butadiene (40), on QH5 QH5 C 6H 5n Me 2NH 0 2N - Me 2NH 0 2N Η (34) CoH 5v 0 2N - F H NMe2 (36) (35) ,Br C 6H 5> Br 2 0 2N " NMe2 (37) 0 2Ν ' NMe2 (38) C ^ Br 2, o H C5H5N 021ΝΓ NMe2 (39) C.
Dichloride (57) was converted smoothly into diiodide (56) with sodium iodide in acetone, probably by way of an S^2' process rather than by elimination-addition. 63 Treatment of the diiodide with zinc-copper couple in ether gave an iodinefree polymer which appears to contain cyclobutene residues. Similarly, diiodide (56) eliminated iodine under both photolytic and thermolytic conditions, but no product definitely attributable to 1,2,3,4-tetrafluorocyclobutadiene (58) was isolated. 63 Reaction of diiodide (56) with phenyllithium under a variety of conditions afforded only amorphous brown products and no evidence pointing to the formation of the desired product, l,2-difluoro-3,4diphenylcyclobutadiene (59) was obtained.
4S The following reagents were found to be ineffective in the dehalogenation of cw-3,4-dichloro-l,2,3,4-tetramethylcyclobutene (52) to 1,2,3,4-tetramethylcyclobutadiene (54): (a) sodium iodide in acetone, (b) sodium in dioxane, (c) magnesium in ether, and (d) magnesium-magnesium iodide in ether. s-3,4-diiodo-l,2,3,4-tetramethylcyclobutane (53) with mercury or silver powder gave air-sensitive products of unknown structure rather than the expected dimer of tetramethylcyclobutadiene (54). Doubts have been expressed concerning the generation of tetramethylcyclobutadiene in C.