SYNTHESIS OF POLYFUNCTIONAL STABLE NITRILE OXIDES OF THE THIOPHENE SERIES AND THEIR RELATIVE REACTIVITIES IN 1,3-DIPOLAR CYCLOADDITION WITH STYRENE

Article abstract of DOI:10.1007/BF00473862

Stable 2-alkylthio- and 2-alkylsulfonylthiophene-3-carbonitrile oxides that contain various functional groups in the 4 and 5 positions of the thiophene ring (Br, OCH3, SCH3, SO2CH3) were synthesized.It is shown that the introduction of electronacceptor substituents into any position of the ring of thiophene-3-carbonitrile oxides gives rise to acceleration of cycloaddition to styrene.The reactivities of o-substituted thiophene-3-carbonitrile oxides of the thiophene series in 1,3-dipolar cycloaddition reactions are determined by the overall effect of the electronic and steric factors of the substituent.