Cine substitution in fused chlorocyclobutanones by N, S and C nucleophiles. Oxyallyl cations and an unusual dimer formation

Article abstract of DOI:10.1016/0040-4039(90)80103-S

Chlorocyclobutanone 1 was shown for the first time to react with S-, N-, and C-nucleophiles to produce cine substitution products, which apparently arise via an oxyallyl cation species 2. With some nucleophiles, the cine product is accompanied by an unusual dimer involving bond formation between two tertiary carbons.