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61 However, partial allylic inversion was observed in reactions involving E- crotyl 190 '91 193 194 J . , 1981, 22,453. J. Pornet and B. , 1981, 22, 1327. Do Khac Manh Duc, M. Fetizon, I. Hanna, and S. Lazare, Synthesis, 1981, 139. M. Franck-Neumann, D . Martha, and F. Brion, Angew. , Int. Ed. , 1981,20,864. L. Mandell, F. J. Heldrich, and R. A. , Synth. , 1981, 11, 5 5 ; G. Mabon, C. Moinet, and J. Simonet, J. Chem. , Chem. , 1981, 1040. M. B. Rubin, J. A m . Chem. ,1981. 103, 7791. g. '96It can also function as an equivalent of monosubstituted acetylenes because it is possible to alkylate the Diels-Alder adduct via an a-sulphonyl carbanion before elimination.

23 Following R2 R2 ,l, R' Br 2 l . 124The geometry of the product is strongly dependent on the Lewis acid used: aluminium chloride furnishes products of almost exclusive E- configuration, whereas the opposite is observed when titanium tetrachloride is used (as shown in Scheme 47). lZ1 lZ2 lZ3 lZ4 J. A. Miller and G. Zweifel, J. A m . Chem. , 1981,103,6217. Miyaura and A. Suzuki, Chem. , 1981,879. -C. Pommelet, C. Nyns, F. Lahousse, R. MerCnyi, and H. G. Viehe, Angew. , Int. Ed. , 1981,20, 585.

Thakar, and M. S. , 1981, 22, 2301. H. Hommes, H. D. Verkruijsse, and L. Brandsma, J. Chem. ,Chem. , 1981,366. H. Hommes, H. D. Verkruijsse, and L. , 1981, 22,2495. ’18 Trimethylsilylallenes (185) undergo autoxidation to give propargylic hydroperoxides under an atmosphere of oxygen at room termperature. ~” 0 (185) (186) < 10% >go% Reagents: i, 02-py; ii, CrO,(py),; iii, aq. HCI The 2-8silylvinyl sulphoxide (187) undergoes rapid syn- elimination on heating with the formation of an acetylenic bond.

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