6π-Cycloadditions of aryl and new heteroaryl N-sulphinylamines with 2,3-dimethylbuta-1,3-diene: synthesis, kinetics, substituent effects, theoretical calculations, and reaction mechanism
Abstract
A range of new N-sulphinylamine derivatives of heteroaryl rings, including tetrazoles, oxadiazoles, thiadiazoles, thiazoles, and oxazoles is reported. The influence of the –N![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
S
+
–O
−
group on the n.m.r. spectra of the ring to which it is bonded is discussed. The kinetics of the cycloaddition reactions of this group with 2,3-dimethylbuta-1,3-diene have been measured for a series of para-substituted phenyl-N-sulphinylamines and the rates correlated with MNDO calculated HOMO–LUMO separations and Hammett substituent constants.
S
+
–O
−
group on the n.m.r. spectra of the ring to which it is bonded is discussed. The kinetics of the cycloaddition reactions of this group with 2,3-dimethylbuta-1,3-diene have been measured for a series of para-substituted phenyl-N-sulphinylamines and the rates correlated with MNDO calculated HOMO–LUMO separations and Hammett substituent constants.
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