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Matusaak and H. Shechter, Abstracts Papers Am. Chem. ,132, 12P (1957). (69) H. C . Brown, J . H. Brewster and H. Shechter, J . Am. Chem. , 7 6 , 467 (1954). 24 F. SHAFIZADEH oppositions is more stable than the corresponding 1,5-1actone with two bond-oppositions, it may be assumed that the former compound resists the formation of cyclic, intermediate products. Unfortunately, very little is known about the mechanism and kinetics of the hydrolysis of sugar lactones, except for the fact that the reaction proceeds with the retention of configuration.
Nenberger, J. Chem. ,745 (1938). ”7. I22 2. Reaction Mechanism According to Bunton and associate^,^^ the hydrolysis of the methyl and the phenyl a- and 0-D-glycopyranosides proceeds through the unimolecular decomposition of the glycoside’s conjugate acid (protonated glycoside). 123Furthermore, it has been shown that, in an aqueous solution containing H2Ol8 the hydrolysis of the above glycosides results in the cleavage of the hexose-oxygen bond, as shown below, and provides unlabeled phenol and unlabeled meth- Ha -- HO OR H OH + H,O’* - (Fp,8H + HOR HO H OH anol.
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. Chem. ,190,9D (1956). (150) Reference 70, p. 202. 41 FORMATION AND CLEAVAGE OF OXYGEN RINGS I N SUGARS indicates that the hydrolysis of glycosides should also proceed through the same mechanism. 161 It is interesting to note that the dimethyl acetals had long ago been postulated by E. 8~ The deamination of 2-amino-2-deoxy aldonic acids and of 1-amino-1-deoxy alditols results in the formation of intermediate, acyclic, diazonium ions which give a 2,5-(or 1,4-)anhydro derivative (see page 54).
Advances in Carbohydrate Chemistry, Vol. 13 by M. L. (editor) Wolfrom