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Borgnaes, J . Org. , 1973,38,2629. A. Wissner and J. Meinwald, J . Org. , 1973,38, 1697. J. C. Blazeiewski, D. Cantacuzene, and C. C. Wakselman, Tetrahedron, 1973, 29, 4233. Three- and Four-mombered Rings 23 The reaction65of phenyl-lithium with cinnamyl chloride has been found to afford a complex mixture of products including diphenylcyclopropanes ( 109a) NU Scheme 9 (Scheme 10). Products (111H115) are similar to those formed from phenyllithium and 1-halogenobut-2-enes and result either by displacement reactions of phenyl-lithium on cinnamyl chloride or more probably through an intermediate carbene which cyclizes to phenylcyclopropane, this being further arylated with phenyl-lithium.
S. Mariano and R. B. , p. 6114: P. S. Mariano and J. KO. , p. 8670; D. Dekeukeleire,E. C. Sanford, and G. S. Hammond, ibid, p. 7904; G. Griffin, N. S. Bhacca, and J. Perreten, ibid, p. 3427; D. C. Lankin, D. Chihal, G. W. Griffin, and N. S. Bhacca, Tetrahedron Letters, 1973,4009;J. I. Seeman and H. , p. 4409;4413; H. Sato, K. Nakanishi, J. Hayashi and Y. Nakadaira, Tetrahedron, 1973,29,275. Three- and Four-membered Rings 31 Ph (163) a ; R b; R Ph =H = Me (164) 10% 0% 0% 6% 9% 10% Ph A __t (165) I + EtCH=C-COMe (166) ( I 64b) Scheme 15 (167) X = CR, o r 0 (168) Some reactions of interests5 which also involve cyclopropane formation from a propene are shown in Scheme 16.
J. Dolansky, V. Bazant, and V. Chvalovsky, Coll. Czech. Chem. , 1973, 38, 3816. E. Lee and D. W. S. Perkin ZZ, 1973,437. Three- and Four-membered Rings 49 It is, perhaps, worth bearing the above in mind in considering the results of Moss and M a l l ~ n who , ~ ~have ~ examined the possibility of synergism in the addition of dichlorocarbene from (243) to oxygenated cyclohexenes. Earlier, it had been suggested that dichlorocarbene-oxygen co-ordination could be responsible for a three-fold increase in the rate of attack on the double bond, but some evidence to the contrary was presented by Moss and further results have now been reported for the exo-methylenecyclohexanes (245a-d).