Silver Ion-Assisted Ring Expansions in Different Solvent Systems

Authors: MESUT BOZ, HAFİZE ÇALIŞKAN, ÖMER ZAİM

Abstract: 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.

Keywords: Carbene, bicyclic compound, ring opening, ring expansion, vinylic halide

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