Application of (. alpha. -phosphonoacyl)silane reagents to the synthesis of. alpha. -. beta. -unsaturated acylsilanes

Journal Article · Fri Jun 09 04:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00273a007· OSTI ID:7071277

Nowick, J S; Danheiser, R L ^[1]

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1. Massachusetts Institute of Technology, Cambridge (USA)

An efficient and convergent synthetic route to {alpha},{beta}-unsaturated acylsilanes has been developed based on the Horner-Wadsworth-Emmons reaction of ({alpha}-phosphonoacyl)silanes. The Arbuzov reaction of the ({alpha}-iodoacyl)silane 1c with trimethyl phosphite provides access to the phosphonate 2, which can be alkylated by treatment with potassium tert-butoxide and methyl iodide to afford 3. These ({alpha}-phosphonacyl)silane reagents combine smoothly with a variety of aldehydes to furnish {alpha},{beta}-unsaturated acylsilanes 5-13 in good to excellent yield.

• OSTI ID: 7071277
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:12; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
360603 -- Materials-- Properties
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACYLATION
CHEMICAL REACTIONS
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
HYDRIDES
HYDROGEN COMPOUNDS
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC SILICON COMPOUNDS
PHOSPHORUS COMPOUNDS
SILANES
SILICON COMPOUNDS
SYNTHESIS