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

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-bis(bromomethyl)cylohex-1-en at low temperature. Nevertheless, the bromination of 1,2-dimethylenecyclohexane at room temperature gave 1,4 addition product 1,2-bis(bromomethyl)cylohex-1-en as a main product together with 1-bromo-1-(bromomethyl)-2-methylenecylohexane and 3-bromo-1,2-bis(bromomethyl)cyclohex-1-ene. Similarly, high temperature bromination of 1,2-bismethylenecyclohexane gave the radical bromination products (3-bromo-1,2-bis(bromomethyl)cyclohex-1-ene and 3,6-dibromo-1,2- bis(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-bis(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-bis(bromomethyl)cyclohexane and the three brominated product 3-bromo-1,2-bis(bromomethyl)cyclohex-1-ene together with the radicalic tetrabrominated product 3,6-dibromo-1,2-bis(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-bis(bromomethyl)cyclohex-1-ene and 3,6-dibromo-1,2-bis(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

References

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