Several ring expansion products carrying vinylic bromo functionality were synthesized by opening of the geminal dibromobicyclo[n.1.0]alkanes ring. Dibromocarbene was formed from bromoform and potassium tert-butoxide in hexane. Its reaction with various cyclic alkenes was the resultant dibromobicyclo[n.1.0]alkanes. Then, opening was performed using AgNO_3 in various solvent systems, such as acetic acid/DMSO, acetic acid/DMF, CH_3OH/acetone, and H_2O/DMF.
Carbene, bicyclic compound, ring opening, ring expansion, vinylic halide
BOZ, MESUT; ÇALIŞKAN, HAFİZE; and ZAİM, ÖMER
"Silver Ion-Assisted Ring Expansions in Different Solvent Systems,"
Turkish Journal of Chemistry: Vol. 33:
1, Article 8.
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss1/8