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R. Talaty, A . R. Clague, M. 0. Agho, M. N. Deshpande, P. M. Courtney, D. H. Burger. and E. F. Roberts, J. Chem. ,Chem. , 1980,889. W. D. Rudorf, Tetrahedron, 1980,36, 1791. 200This forms the last step in a mild, general method for preparation of oxazolines, starting from the conversion of a wide range of carboxylic acids into their acyl-imidazoles, with subsequent addition of aziridine, to give quantitative yields of the corresponding N-acyl-aziridines (260). 201The cell consisted of a platinum anode and a graphite cathode, using Bun4" C104 in MeOH, CH2C12,or MeCN as the electrolyte; yields of up to 80% have been reported, with low consumption of electricity.
A. Donnelly and D. E. Maloney, Tetrahedron, 1979,35, 2875. 6o 61 J. A. Donnelly and D. E. Maloney, Tetrahedron, 1979, 35, 2883. S. Akabori, M. Ohtomi, and S. Yatabe, Bull. Chem. SOC. , 1980, 53, 1463. 9 J (47) (48) Scheme 6 (49) Two groups, working independently, have simultaneously published descriptions of epoxyannulation procedures, based on intramolecular reactions of sulphur ylides, that are of considerable synthetic importance. , (57) (50%) from 2-carbethoxycyclohexane ( 5 5 ; n = 2). ( C g L ( C G -& ( c a s , , (53) (52) Ph Reagents: i, J, iii , Me,C(OMe),, H', heat; ii, PhSH, AIBN, heat; iii, Et,0+BF4-; iv, Bu'OK Scheme 7 62 63 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. For the oxidation of cyclohexene, a two-phase system was used (water/benzene), with 18-crown-6 as the phase-transfer agent.