Read e-book online Advances in Carbohydrate Chemistry, Vol. 13 PDF

By M. L. (editor) Wolfrom

ISBN-10: 0120072130

ISBN-13: 9780120072132

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Lowry and I. J. Faulkner, J. Chem. ,127,2883 (1925). (143) C. G. Swain and J. F. Brown, J r . , J. Am. Chem. ,74, 2534 (1952). (144) A. M. Eastham, E. L. Blackall and G. A. Latremouille, J . A m . Chem. , 77, 2182 (1955). (145) E. L. Blackall and A. M. Eastham, J. Am. Chem. ,77,2184 (1955). (146) P. A. Levene, A. L. Raymond and R. T. , 96,699 (1932). (147) D . F. , and G. R. Ferrante, J. Am. Chem. , 76,4103 (1954). (148) D . F. , J. Am. Chem. ,77, 1667 (1955). (149) D. F. Mowery, J r . , Abstracts Papers Am.

44 F. sHAFIZADEH this decomposes to a carbonium ion, which affords an alcohol of predominantly inverted configuration plus some olefins. The reaction proceeds through the SN1mechanism, and complete racemization is prevented by a masking effect of the departing group. lG0The formation of these compounds was explained on the basis of an intermediate, carbonium ion. In more complicated compounds, variations in the steric configuration of the molecule and the nature of the neighboring groups may lead to the rearrangement of carbon bonds as well as to elimination and displacement products.

65) J . C. , 12, 35 (1957). (66) W. Schnelle and B. Tollens, A n n . 61 (1892). ^^ According to these authors, in the idealized, planar-ring structure of cyclepentane (XI), there is a substantial strain resulting from ten bond-oppositions; introduction of a carbonyl group, which assumes a staggered conformation (XII) with respect to the neighboring bonds, stabilizes the ring by XI (10-bond opposition; 10 Kcal. strain) XI1 (6-bond opposition; 6 Kcal. strain) diminishing the number of bond oppositions to six.

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Advances in Carbohydrate Chemistry, Vol. 13 by M. L. (editor) Wolfrom

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