Download e-book for kindle: Alicyclic Chemistry Vol. 3 by W Parker;

By W Parker;

ISBN-10: 0851865526

ISBN-13: 9780851865522

ISBN-10: 1847555462

ISBN-13: 9781847555465

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Amer. Chem. , 1973,95, 3957. Alicyclic Chemistry 34 (184) R = NHCOMe (183) a; R = H b; R = NHCOMe C: R = OAC p p OMe (183) --% Scheme 17 35 Three- and Four-membered Rings I Scheme 18 believed to occur by a Norrish Type I cleavage to the 1,5-biradical(l89)which subsequently rearranges to the isocyanato-1,3-biradical(190) before ring closure (Scheme 18). Preliminary experiments on the photolysis of y-sultones (192) suggest that these might provide a useful new route to cyclopropanes in an elimination reaction which parallels the behaviour of y - l a c t ~ n e s .

Org. , 1973,38,2243. J. A. Connor and J. P. S. Perkins Z , 1973, 17. H. Berke and E. Lindner, Angew. Chem. Internat. , 1973,12,667. 55 Three- and Four-membered Rings LM(CO)5 + - Ph,P=C=C=O M = C r o r W ; L = MeCN M = M o ; L = CO c//O (CO),M-C/( 'PPh, (278) Scheme 31 From Diazo-compounds. 152 The reactions of diphenylcarbene, generated photochemically from the diazoalkane, with olefins and acetylenes have been studied in detail. The carbene reacts by both addition and abstraction, the partitioning between these paths being determined by steric factors which favour cyclopropane formation for the less-substituted olefins.

Ar ~:pmw + *j=( H Z - HV COMe M Z (92) a; Y = Z = CN b; Y = Z = C0,Et c ; Y = CN,Z = C0,Me (94) (93a) R’ (95) ’’ A. Foucaud and E. Corre, Bull. chim. France, 1973, 1514. 58 A. Padwa and W. Koehn, J . Org. , 1973,38,4007. e Hvc Me Ar Z (93W Three- and Four-membered Rings 21 Small quantities of the dimeric spiro-adduct (99) were detected in addition to the major products (97) and (98) when the isoxazolones (96) were treated with benzonitrile oxide. The yield of (99) was related to the reaction temperature and increased in proportion to the evolution of nitric oxide.

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