Syntheses of [omega]-alkynyl aldehydes and ketones via oxidation of [omega]-alkynyl alcohols with pyridinium dichromate

Journal Article · Fri Jan 01 04:00:00 EST 1988 · Organic Preparations and Procedures International; (United States)

DOI:https://doi.org/10.1080/00304948809355869· OSTI ID:5526476

Bierer, D E; Kabalka, G W ^[1]

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1. Univ. of Tennessee, Knoxville, TN (United States)

Pyridinium dichromate (PDC) is an effective reagent for the oxidation of alcohols and a number of modifications of the original procedure have been reported. Interestingly, PDC has never been used to oxidize non-conjugated acetylenic alcohols. As a part of a project involving the chemical preparation of a number of unsaturated amino acids, the authors investigated the synthesis of a series of [omega]-alkynyl aldehydes. The authors now report that the PDC oxidation of [omega]-alkynyl alcohols is an effective route to the corresponding [omega]-alkynyl carbonyl compounds.

• DOE Contract Number: FG05-86ER60434
• OSTI ID: 5526476
• Journal Information: Organic Preparations and Procedures International; (United States), Journal Name: Organic Preparations and Procedures International; (United States) Vol. 20:1; ISSN 0030-4948; ISSN OPPIAK
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
ALDEHYDES
ALKYNES
AMINES
AMMONIUM COMPOUNDS
AZINES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHROMIUM COMPOUNDS
DICHROMATES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
HYDROXY COMPOUNDS
KETONES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDATION
OXYGEN COMPOUNDS
PYRIDINES
PYRIDINIUM COMPOUNDS
QUATERNARY COMPOUNDS
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS