Catalytic conversion of. beta. -hydroxy carboxylic acids to olefins by tungsten(V) complexes: A new acyl group transfer catalyst
- Princeton Univ., NJ (United States)
Oxotungsten tetrachloride catalyzes the conversion of {beta}-hydroxy carboxylic acids to olefins, in the presence of base. The reaction proceeds in high yield, stereospecifically, and with high catalyst turnover. Examination of the likely stoichiometric steps for {beta}-hydroxy carboxylic acid activation shows the formation of intermediate chelates, structures of which were studied by {sup 1}H NMR. The role of the base was probed by using both {sup 1}H and {sup 183}W NMR, and it was shown that base simply deprotonates the chelate; base does not coordinate to the W center. {beta}-Lactones were the initial products of this sequence from which decarboxylation occurred to give the olefinic product.
- OSTI ID:
- 6070333
- Journal Information:
- Organometallics; (United States), Journal Name: Organometallics; (United States) Vol. 9:12; ISSN 0276-7333; ISSN ORGND
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALKENES
CARBOXYLIC ACIDS
CATALYTIC EFFECTS
CHELATES
CHEMICAL PREPARATION
COMPLEXES
HYDROCARBONS
LIGANDS
NMR SPECTRA
ORGANIC ACIDS
ORGANIC COMPOUNDS
REFRACTORY METAL COMPOUNDS
SPECTRA
STEREOCHEMISTRY
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS
TUNGSTEN COMPOUNDS