93796-39-5Relevant articles and documents
Chemistry of 5-ylidene-1,3-dioxolan-4-ones. Syntheses of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO)
Ramage,Rose,Macleod
, p. 4877 - 4880 (1988)
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Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols
Ramage, Robert,Griffiths, Gareth J.,Shutt, Fiona E.,Sweeney, John N. A.
, p. 1531 - 1537 (2007/10/02)
2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).