CONCERNING THE REACTION OF ANTI-BENZENE DIOXIDE WITH VARIOUS NUCLEOPHILES

trans-3,4:5,6-Diepoxycyclohex-1-ene (anti-benzene dioxide) (5) was bro ught into reaction with several S, O, and C nucleophiles. S and O nucl eophiles gave the bis-adducts stemming from independent reaction of th e two epoxy functions. C nucleophiles, on the other hand, led to 1,4-a ddition products. A deuterium labelling experiment showed that BuLi ad ded to the vinyloxirane part of 5 rather than to the conjugated diepox ide function, yielding the cis-adduct. Cuprates gave - as expected - p redominatly the trans-products.