Anhydro-osazones: mass spectra, and direct formation from glycosuloses and hydrazines

Document Type

Article

Publication Date

1-1-1973

Abstract

The mass spectra of Diels 3,6-monoanhydro-osazones, Percival dianhydro-osazones, and our own type of dianhydro-osazones show markedly different fragmentation patterns. This behavior was used to identify 3,6-anhydro-D-arabino-hexosulose 1-(phenylhydrazone) 2-(methylhydrazone) (2) in the reaction products of D-arabino-hexosulose 1-(phenylhydrazone) with methylhydrazine, and a dianhydro-osazone (4) of the Percival type among the products of reaction of D-arabino-hexosulose with 2-hydrazinopyridine. The anhydro-osazones were separated from the nondehydrated osazones by chromatography. N.m.r-spectral and c.d. studies revealed that, owing to the small size of the methyl group, compound 2 retained the D-arabino configuration during cyclization, and is thus the first anhydro-osazone of the Diels type that has the two bulky, hydrazone residues and the 4-hydroxyl group on the same side of the anhydro ring. © 1973.

Publication Title

Carbohydrate Research

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