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ChemInform Abstract: Reactions of Oxazolinium and Dihydrooxazinium Salts Prepared by an Azide Insertion Sequence: pH Control of Product Distribution.

✍ Scribed by J. E. FORSEE; B. T. SMITH; K. E. FRANK; J. AUBE


Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Reactions of Oxazolinium and Dihydrooxazinium Salts Prepared by an Azide Insertion Sequence: pH Control of Product Distribution. -Ketones (I) and (V) undergo a Lewis acid mediated reaction with azido alcohols (II) to form intermediate imidate salts. Hydrolytic workup of the reaction mixtures leads either to lactams/amides (III) and (VI) or lactones/esters (IV) and (VII) according to the pH of the medium used for hydrolysis. -