STEREOCHEMISTRY .77. STRUCTURE OF THE IN3 ADDUCT OF 1-PHENYLCYCLOHEXENE - ITS CHEMISTRY AND CH COUPLING AS A DIAGNOSTIC-TOOL

The addition of iodine azide to alkenes, discovered by Hassner et al.,2 is by now a well-established method for stereo- and regiospecific introduction of nitrogen functional groups.2 In a recent paper, Sivasubramanian et al.3 claimed that the regiochemistry of the IN3 addition to 1-aryl-l-cyclohexenes was the reverse of that usually observed for conjugated aromatic alkenes. Thus, the IN3 adduct of 1-phenylcyclohexene, originally assigned structure 1 by Hassner et al.,4was claimed to be instead the tertiary iodide 2.3 The unsaturated azide obtained on dehydroio-dination of the adduct with hot KOH in ethanol was assigned structure 3.3. © 1990, American Chemical Society. All rights reserved.