Synthesis and methylation of (1R)-9,9-dimethyltricyclo[6.1.10.2,6]deca-2,5-diene(5)

Authors

  • G.U. Obuzor Department of Pure and Industrial Chemistry, University of Port Harcourt, Rivers State, Nigeria Author
  • B.L. Booth Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester M60 1QD, UK. Author

Keywords:

Synthesis, Methylation, Chiral Ligand

Abstract

 The new thermally stabilized chiral ligand (1R)-6,9,9-trimethyltricyclo[6.1.1.0]deca-2,5-diene (6) has
 been prepared from the (now room temperature stable) chiral ligand (IR)-9,9-dimethyltricyclo
 [6.1.1.0]deca-2,5-diene (5) hence establishing (5) as a viable diene for further reactions.  A variation in
 reaction temperature has been used to advantage for the stereocontrolled preparation of the chiral (3) by
 the treatment of the tosylate (2a) or the mesylate (2b) at 110 oC for 4hr in DMF lead to the synthesis of
 the new room temperature stable 2-vinyl-6,6-dimethylbicyclo[3.1.1]-2-hept-2-ene (3) in a higher yield
 (89%) and to the kinetically stable product which does not dimerise at room temperature.

Published

2025-02-25

Issue

Vol. 2 No. 1 (2005): ChemClass Journal

Section

Articles