Free-radical carbonylation. Efficient trapping of carbon monoxide by carbon radicals
- Osaka Univ. (Japan)
The authors examined the AIBN-induced radical reaction of n-octyl bromide (1) (Scheme 1) with Bu{sub 3}SnH under CO pressure in hope of trapping of carbon monoxide by octyl radical followed by hydrogen abstraction from tin hydride. When the reaction on a 0.5-mmol scale was conducted under CO pressure, using an autoclave with an inserted glass tube (5 mol % of AIBN, benzene (10 mL), 80{degree}C, 3 h), the desired aldehyde 2 was obtained together with n-octane (3), formed via simple reduction of 1. Surprisingly, this radical/CO trapping sequence proceeds even at 15 atm of CO pressure to give 2 in 38% yield (run 2). Generally, higher pressures of CO resulted in the increase of 2. These results demonstrate that the control of the relative concentrations of CO to tin hydride is an important factor to effect the CO trapping leading to aldehyde 2.
- OSTI ID:
- 6835354
- Journal Information:
- Journal of the American Chemical Society; (USA), Vol. 112:3; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
36 MATERIALS SCIENCE
CARBON MONOXIDE
TRAPPING
RADICALS
CARBONYLATION
ACYL RADICALS
DATA ANALYSIS
EXPERIMENTAL DATA
MEASURING INSTRUMENTS
MEASURING METHODS
MEDIUM PRESSURE
MEDIUM TEMPERATURE
TIN HYDRIDES
CARBON COMPOUNDS
CARBON OXIDES
CHALCOGENIDES
CHEMICAL REACTIONS
DATA
HYDRIDES
HYDROGEN COMPOUNDS
INFORMATION
NUMERICAL DATA
OXIDES
OXYGEN COMPOUNDS
TIN COMPOUNDS
400201* - Chemical & Physicochemical Properties
360104 - Metals & Alloys- Physical Properties