Fragmentation of carbohydrate anomeric alkoxyl radicals. A new synthesis of chiral beta-iodo azides, vinyl azides, and 2H-azirines.
[reaction: see text] The reaction of 3-azido-2,3-dideoxy-hexopyranose compounds from the d-gluco, d-galacto, d-lacto, and l-arabino carbohydrate series, with (diacetoxyiodo)benzene and iodine, generated 2-azido-1,2-dideoxy-1-iodo-alditols with one carbon less than the starting carbohydrate. These beta-iodo azides could be transformed by dehydroiodination into vinyl azides, which in turn afforded 3-monosubstituted 2H-azirines under thermal conditions. These beta-iodo azides and 2H-azirines may be interesting chiral synthons for the preparation of more complex heterocyclic systems.
D000438:Alcohols / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis*; D001389:Azirines / Q000138:chemical synthesis*; D002241:Carbohydrates / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis
D000438:Alcohols; D001386:Azides; D001389:Azirines; D002241:Carbohydrates; D006847:Hydrocarbons, Iodinated; D014753:Vinyl Compounds; C059688:alkoxyl radical