4630-83-5Relevant academic research and scientific papers
First examples of the selective carbonylation of C6-C10 linear alkanes to tertiary carbonyl-containing compounds
Akhrem, Irena S.,Afanas'eva, Lyudmila V.,Vitt, Sergei V.,Petrovskii, Pavel V.
, p. 180 - 182 (2007/10/03)
The carbonylation of C6-C10 n-alkanes with CO in the presence of CBr4·2A1Br3 at -40°C and 1 atm CO leads to the products of non-destructive carbonylation, i.e., the esters of tertiary carboxylic acids, R1/
Regioselective 6-endo cyclization of 5-carbomethoxy-5-hexenyl radicals: A convenient synthesis of derivatives of the 1-azabicyclo[2.2.1]heptyl system
Della, Ernest W.,Kostakis, Chris,Smith, Paul A.
, p. 363 - 365 (2008/02/13)
(equation presented) Ring closure of the 5-carbomethoxy-5-hexenyl radical is governed largely by the polar effect, and as predicted by frontier molecular orbital considerations, endo cyclization predominates, leading to cyclohexyl rather than cyclopentyl-based products. In cyclization of the corresponding β-ammonio species 18, stereoelectronic effects do not distinquish between attack of the radical center at C3 or C4, each of which represents a 5-exo ring closure. The radical 18 is found to cyclize with great rapidity and with high stereoselectivity to give bicyclo[2.2.1]heptane products in accordance with expectation based on polar effects; this transformation represents an excellent entry to the physiologically important bicyclic ester 17.
