Bromination of 1,2-Dimethylenecyclohexane: Temperature Effect on Product Distribution

Authors : Aliye ALTUNDAS

Pages : 815-821

Doi:10.35378/gujs.466697

View : 16 | Download : 8

Publication Date : 2019-09-01

Article Type : Research Paper

Abstract :In this study the electrophlic addition of bromine to an exocyclic diene, 1,2 dimethylenecyclohexane, was investigated. The bromination of 1,2-dimethylenecyclohexane yielded 1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cylohex-1-en at low temperature. Nevertheless, the bromination of 1,2-dimethylenecyclohexane at room temperature gave 1,4 addition product 1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cylohex-1-en as a main product together with 1-bromo-1-insert ignore into journalissuearticles values(bromomethyl);-2-methylenecylohexane and 3-bromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene.  Similarly, high temperature bromination of 1,2-bismethylenecyclohexane gave the radical bromination products insert ignore into journalissuearticles values(3-bromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene and 3,6-dibromo-1,2- bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene); in addition to the 1,4 addition product. While the bromination of exocylicdiene at room temperature with excess bromine gave  tetrabrominated product 1,2-dibromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohexane as a sole product, the bromination of exocyclicdiene in high temperature with excess bromine resulted in a tetra brominated product 1,2-dibromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohexane and the three brominated product 3-bromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene together with the radicalic tetrabrominated product 3,6-dibromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene as  main products. However, the high temperature bromination of 1,4 brominated product with excess bromine provided only the radicalic brominated product 3-bromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene and 3,6-dibromo-1,2-bisinsert ignore into journalissuearticles values(bromomethyl);cyclohex-1-ene.Thus the functional agents which can be used as starting material in the synthesis of many compounds were synthesized, purified and characterized.
Keywords : Bromination, 1, 2 dimethylenecyclohexane, high temperature bromination