TY - JOUR
T1 - 1,3-dipolar cycloadditions of cyclic nitrones with trisubstituted alkenes
AU - Ali, Sk Asrof
AU - Wazeer, Mohammed I.M.
PY - 1990
Y1 - 1990
N2 - A study of the regio- and stereo-chemical behaviour of the 1,3-dipolar cycloaddition of a series of trisubstituted alkenes with the cyclic nitrones 1-pyrroline 1-oxide (1) and 3,4,5,6-tetrahydropyridine 1-oxide (2) has been carried out. Regio- and stereo-selectivity in these cycloadditions have been explained in terms of maximum overlap of frontier orbitals, steric encumbrance, and secondary orbital interactions. The activation parameters and the effect of solvent on the rate constant for the addition reaction of a highly polarized alkene indicate the concerted nature of the reaction. The nitrone (2) is found to be more reactive than the nitrone (1) in all of these additions.
AB - A study of the regio- and stereo-chemical behaviour of the 1,3-dipolar cycloaddition of a series of trisubstituted alkenes with the cyclic nitrones 1-pyrroline 1-oxide (1) and 3,4,5,6-tetrahydropyridine 1-oxide (2) has been carried out. Regio- and stereo-selectivity in these cycloadditions have been explained in terms of maximum overlap of frontier orbitals, steric encumbrance, and secondary orbital interactions. The activation parameters and the effect of solvent on the rate constant for the addition reaction of a highly polarized alkene indicate the concerted nature of the reaction. The nitrone (2) is found to be more reactive than the nitrone (1) in all of these additions.
UR - https://www.scopus.com/pages/publications/37049082822
U2 - 10.1039/p29900001035
DO - 10.1039/p29900001035
M3 - Article
AN - SCOPUS:37049082822
SN - 0300-9580
SP - 1035
EP - 1039
JO - Journal of the Chemical Society. Perkin Transactions 2
JF - Journal of the Chemical Society. Perkin Transactions 2
IS - 6
ER -