Studies on the reactivity of (pentitol-1-yl)nitrocyclohexadienes with acetyl chloride in methanol

✍ Scribed by M. Baños; E. Román; J.A. Serrano

• Publisher: Elsevier Science
• Year: 2003
• Tongue: English
• Weight: 362 KB
• Volume: 14
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(03)00155-1

✦ Synopsis

Pentitol-1-yl)nitrocyclohexadienes with pentaacetylated D-galacto and D-manno sugar side-chains react in different ways when they are subjected to transesterification with acetyl chloride in methanol. Although both processes should commence with a deacetylation, subsequent intramolecular nucleophilic attack from the resulting hydroxyl groups on electrophilic carbons on the cyclohexadiene ring was dependant on the nature of the sugar side-chain, as well as on the configuration at the stereogenic carbon of the cyclohexadiene ring. Thus, D-manno nitrocyclohexadiene led to a complex mixture from which we could either isolate or identify products with dioxatricyclodecane dimethyl ketal, benzofuran, chromane-3,4-diol, bicyclic or tricyclic oximes, nitrobenzene, and nitrocyclohexenol structures. In contrast, D-galacto nitrocyclohexadiene led exclusively to a bicyclic oxime.