Date of Award
Honors Thesis (Open Access)
Colby College. Chemistry Dept.
Dasan M. Thamattoor
Jeffrey L. Katz
This thesis is the first report of reactions of atomic carbon with acid chlorides. Carbon is known to react with phosgene to afford dichlorocarbene. We report a similar reaction with carbon and acid chlorides, generating alkylchlorocarbenes. We examine both the nature of the carbene products generated through deoxygenation and the general reactivity of carbon with the acid chlorides. We report two ways in which carbon reacts with acid chlorides. First, as expected from prior work with phosgene, carbon deoxygenates the carbonyl group yielding alkylchlorcarbenes, which rearrange as expected. Second, carbon abstracts the chlorine, and generates the acyl radical, which, in the case of pivaloyl chloride and isobutyryl chloride decarbonylates and a free radical chain reaction mechanism generates the alkyl halide. The reaction of isobutyryl chloride and carbon demonstrates that both the deoxygenation and chlorine abstraction mechanisms compete, as there is a 2:1 ratio of the two processes, respectively.
Carbon, Chlorides, Acids, Fullerenes, Reaction
Recommended CitationHerrick, Daniel B., "Reactions of Atomic Carbon with Acid Chlorides" (2008). Honors Theses. Paper 240.
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