Oxidation of alkynes by hydrogen peroxide catalyzed by methylrhenium trioxide

Journal Article · Thu Nov 30 23:00:00 EST 1995 · Journal of Organic Chemistry

DOI:https://doi.org/10.1021/jo00129a010· OSTI ID:471559

Zhu, Zuolin; Espenson, J H ^[1]

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1. Ames Lab., IA (United States)

The oxidation of alkynes with hydrogen peroxide is catalyzed by methylrhenium trioxide. The reactions can be rationalized by postulating that an oxirene intermediate is formed between a rhenium peroxide and the alkyne. Internal alkynes yield {alpha}-diketones and carboxylic acids, the latter from the complete cleavage of the triple bonds. Rearrangement products were observed only for aliphatic alkynes. Terminal alkynes gave carboxylic acids and their derivatives and {alpha}-keto acids as the major products, but their yields varied with the solvent used. 5 tabs.

• Sponsoring Organization: USDOE
• DOE Contract Number: W-7405-ENG-82
• OSTI ID: 471559
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 24 Vol. 60; ISSN 0022-3263; ISSN JOCEAH
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
ALKYNES
CATALYTIC EFFECTS
CHEMICAL REACTION YIELD
HYDROGEN PEROXIDE
ORGANOMETALLIC COMPOUNDS
OXIDATION
REDUCTION
RHENIUM COMPLEXES