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

By M. L. (editor) Wolfrom

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Nevertheless, there is a strong possibility that this decrease in the rates of reaction may be due to the respective polar effects of the -CH3, -CH20H, and -CHOH--CHzOH substituents, as noted for methyl 6-deoxy-a- and @-L-mannopyranoside. IV. NITROUSACID DEAMINATION OF AMINOSUGARS Nitrous acid deamination of simple aliphatic primary amines involves, according to Ingold and c ~ w ~ r k ean r ~intermediate ,~ ~ ~ diazonium ion; (155) A. B. Foster and W . G. Overend, Chem. & I n d . (London), 566 (1955).

Chem. , 69, 1170 (1937). (89) C. B. Purves, J . Am. Chem. ,66, 1969 (1934). 9 2. 4 5. 1 9. 5 46. 98 X lo-' min-I). The numbers represent the position OII which the substituent is axial. In the terminology suggested by Reeves, the normal chair conformat,ion is denoted by CZ for D sugars and 1C for L sugars. d Indirectly obtained value. 0 1,3,4 A2,5 p anomer 3. 9 X lo-' min-') under the above reaction conditions. b The numbers represent the position on which the substituent is axial. c In the terminology suggested by Reeves, the normal chair conformation is denoted by C1 for D sugars and 1C for L sugars.

S. Isbell and H. L. Frush, J . Research Natl. Bur. Standards, 24,125 (1940). (84) F. Shafizadeh and A. Thompson, J . Org. , 21, 1059 (1956). (85) The relative positions of C1 and C2 are shown according t o M. S. Newman, J . Chem. 32, , 344 (1955). (86) L. J . Heidt and C. B. Purves, J . Am. Chem. ,66, 1385 (1944). (87) E. A. Moelwyn-Hughes, Trans. ,26, 503 (1929). (88) C . B. Purves and C. S. Hudson, J . A m . Chem. , 69, 1170 (1937). (89) C. B. Purves, J . Am. Chem. ,66, 1969 (1934). 9 2. 4 5.

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