ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Esters of carboselenoic acids, formed from carboxylic acids by conventional methods, undergo reaction with tributyltin hydride in inert aromatic solvents, either by heating to give the corresponding aldehyde or the corresponding alkane depending on reaction temperature and the structure of the parent carboxylic acid, or by ultraviolet irradiation at ambient temperature when the aldehyde is formed predominantly in high yield. In the case of esters of α, β-unsaturated carboselenoic acids the thermal reaction leads only to the corresponding aldehyde.The above stannane reduction can also be applied to selenocarbonates of primary and secondary alcohols (prepared from the corresponding chloroformates), to give the alkane, the parent alcohol and the corresponding formate, in relative amounts depending on the reaction temperature.These reactions thus constitute preparatively useful and high-yield degradation methods compatible with the presence of many other functional groups.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19800630823