37464-84-9Relevant academic research and scientific papers
β-Functionalised radicals in organic synthesis: 2-Acyloxyalkyl radicals from 2-acyloxyalkyl iodides by the tin route
Foubelo, Francisco,Lloret, Francisco,Yus, Miguel
, p. 5131 - 5138 (1994)
The reaction of iodoesters 1a-c with electrophilic olefins 2a-d and in situ generated tributyltin hydride (from a substoichiometric amount of tributyltin chloride and an excess of sodium borohydride) in the presence of a catalytic amound of AIBN in ethanol at 0 to 20°C yields the expected coupling products 3aa-3cd. Products 4 resulting from an iodine/hydrogen exchange are also obtained as by-products in variable amounts. The stereochemistry of the coupling reaction is studied: starting from trans-2-iodocyclohexyl acetate (1d) and methyl acrylate (2a) a 1/3 mixture of the corresponding cis/trans diastereoisomers is obtained. This result indicates that the corresponding radical coupling is not stereospecific.
