ChemInform Abstract: Generation and Trapping of ortho-Substituted Thionitrosobenzenes: Competitive Diels-Alder and Ene Reactions with Dimethylbutadiene

Transient thionitrosoarenes, ArN=S, (2) that bear a substituent (CN, Br or Me) ortho to the reactive N=S group have been generated by two entirely different routes and intercepted with dimethylbutadiene to afford mixtures of Diels-Alder and ene adducts, (3) and (4), respectively; the ene adduct predominates for each system.