By M. L. (editor) Wolfrom
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2846 (1949). (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.
Cyclic (XXXV) or of an acyclic (XXXIX) carbonium ion-with rapid, subsequent stages, as shown in Fig. 1. At present, there is no general or conclusive proof in favor either of the cyclic or of the acyclic pathways. However, there is much circumstantial evidence indicating the cleavage of the oxygen ring and the formation of an acyclic intermediate, particularly for the reactions involving the interconversion of furanosides and pyranosides. This mechanism accounts for the formation of ethyl l-deoxy-lthio-a-D-glucopyranoside (XLVI), ethyl 1-deoxy-1-thio-P-D-glucopyranoside (XLVII), the reducing sugar (XLIV), and a lesser amount of ethyl 1-deoxy-1-thio-0-D-glucofuranoside(XLV) from the hydrolysis of ethyl 1-deoxy-1-thio-a-D-glucofuranoside (XLIII) as described previously (see page 31).
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