Abstract
Abstract 2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) reacted with diazoethane to give stereoisomeric bicyclic diones (3, isomer ratio=3.4) arising from dipolar addition to the C=C bond of DDQ. DDQ reacted with phenyldiazomethane to afford also stereoisomeric bicyclic diones (7) in the ratio of 5:1, together with stilbenes (8). On the other hand, DDQ gave the (ethenyloxy)benzene derivative (14) with 1-phenyldiazoethane. The formation of 8 and 14 was interpreted by considering the participation of 1:1 betaines resulting from addition to the C=O bond. The added methanol captures the betaines, thus giving rise to dimethyl acetals of benzaldehyde and acetophenone, along with 2,3-dichloro-5,6-dicyanohydroquinone. These reactivities of DDQ were discussed in comparison with those of chloranil.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
