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A mild cleavage of 1,3-diketones: Preparation of 2-acyl-1,3-dithianes

โœ Scribed by Robert J. Bryant; Edward McDonald

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
70 KB
Volume
16
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A mild method for cleaving 1,3-diketones is described. The products are 2-acyldithianes and these R-Csynthons can be alkylated under mildly basic conditions. Acetylacetone (1) reacted with propane-1,3-dithio tosylate (2) in methanol to give 2-acetyl-1,3-dithiane + (3) (82%), whose 'H-n.m.r. spectrum showed a characteristic singlet at 6 4.05. Similar treatment of cyclohexane-1,3-dione (4) gave the keto-ester (5) (93%).

๐Ÿ“œ SIMILAR VOLUMES

Unexpected reactivity of oxygenated 2-ac
Unexpected reactivity of oxygenated 2-acyl-1,3-dithianes with electrophiles
โœ Michael Smietana; Alain Valleix; Charles Mioskowski ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 208 KB

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