ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Stereochemistry of anhydrohexoses
Research Institute of Food Industry, Bratislava
Abstract: A survey of published work suggests the following rules concerning the structure and properties of anhydrohexoses: Hexose 6-halohydrins in alkali give 3,6-anhydrohexoses, with elimination of H halide. The products have the cis-bicyclo [3.3.0]octane structure, viz., two fused furanose rings, as might in most cases be expected on steric grounds. The 3,6-anhydrohexoses do not exhibit mutarotation, and they give a pos. Schiff reaction. The above formulation is possible only when the 3- and 4-OH groups of the parent hexose are in the trans position. In the case of 3,6-anhydrogalactose, in which these groups are in the cis position, the fused furanose ring structure is impossible, and a free aldehyde or a fused pyranoid ring structure can result. Their tautomeric change leads to mutarotation. Hudson's rules concerning the optical rotation of benzylphenylhydrazones and phenylhydrazides of 3,6-anhydrohexonic acids are extended to the 3,6-anhydrohexoses.
Full paper in Portable Document Format: 15a134.pdf (in Slovak)
Chemical Papers 1 (5) 134–148 (1947)