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a review of the literature abstracted between July 1980 and by H Suschitzky; O Meth-Cohn; Great Britain. The Royal Society

By H Suschitzky; O Meth-Cohn; Great Britain. The Royal Society of Chemistry

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M. Chen, and S. Lee, J. Org. , 1980,45,2096. J. A. Marshall and J. A. Kerschen. Synth. , 1980,10,409. I. M. Maione, and A. Calcagni, J. Chem. , Perkin Trans. 1, 1980,440. "' Using HC10, in THF, a 6p-OAc group completely blocked cleavage of both the a- and p-epoxides, and a 6a-OAc group retarded ring-opening compared with (130; R' = R2 = H). "~ The mechanism was found to be SN2-like, with all positional isomers that were formed in the AlC1,-catalysed reaction of epoxypropane having almost completely inverted configurations at the epoxide carbon.

Wade, J. Org. , 1980,45, 5328. G . Alvernhe, S. Lacombe, and A. , 1980,21,289. R. T. Coults, A. Benderly, and A. L. C. Mak, J. , 1980,16, 277. H. Koyama, J. Chem. , Perkin Trans. 2, 1981, 121. '~~ This material was found to transport adenine, amino-acids, and simple amine derivatives efficiently through artificial membranes. It behaved similarly to dibenzo-18-crown-6 except that a high specificity was demonstrated towards aromatic amines. Formation of Other Ring Systems from Aziridines. 19' Pyrrolinones (256) are obtained when LiC-CMe reacts with (250; R', R2 = But, 1-adamantyl) in THF, at room temperature, under nitrogen.

86 A. Nishinaga, H. Tomita, Y. Tarumi, and T. , 1980,21,4849. '' J. , and R. , 1980,21,2491. A. J. Biloski, R. P. Heggs, and B. 810. " This epoxide mixture is the source of quinone epoxide (103) (100%) by a retro-Diels-Alder reaction that takes place in a sealed tube at 160-180°C. Partial reduction of (102) with NaBH, before it is heated in a sealed tube leads to a mixture of cyclohexenones (104) ( 100OO/ ). " This system forms the basis of a new generalized method that is capable of giving high yields of epoxides from either (E)- or (2)-cinnamic acids with retention of configuration.

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