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New and improved methods for the radical decarboxylation of acids

Journal of the Chemical Society Chemical Communications · 1983 · pp. 939–939

D. H. R. BARTON✉(Institut de Chimie des Substances Naturelles)David Crich(Institut de Chimie des Substances Naturelles)William B. Motherwell(Institut de Chimie des Substances Naturelles)

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Abstract

Carboxylic acid esters derived from N-hydroxypyridine-2-thione undergo efficient radical chain decarboxylation to the corresponding nor-alkane on treatment with either tri-n-butylstannane or t-butylmercaptan; in the absence of these hydrogen atom donors a smooth decarboxylative rearrangement giving noralkyl 2-pyridyl sulphides is observed.

Radical Photochemical Reactions Sulfur-Based Synthesis Techniques Oxidative Organic Chemistry ReactionsDecarboxylationChemistryAlkaneHydrogen atomMedicinal chemistryHydrogenCarbon atomOrganic chemistryStereochemistryCatalysis

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