Improving the yield of the exhaustive grignard alkylation of N-benzylphthalimide

Jayawardena, Viraj, Fairfull-Smith, Kathryn E., & Bottle, Steven E. (2013) Improving the yield of the exhaustive grignard alkylation of N-benzylphthalimide. Australian Journal of Chemistry, 66(6), pp. 619-625.

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Abstract

The tetraalkylation of N-benzylphthalimide is the major yield limiting step in the common synthetic route to isoindoline nitroxides. The progress of this reaction was found to be limited by the formation of previously unobserved mono- and dialkyl side products that do not lead to the desired product. The yield for the tetraalkylation of N-benzylphthalimide with ethylmagnesium iodide could be increased (60% over 2 steps) when a step-wise addition sequence was employed. The new two step synthesis offers a practical preparative scale alternative to the current approach.

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ID Code: 58991
Item Type: Journal Article
Refereed: Yes
DOI: 10.1071/CH12528
ISSN: 0004-9425
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > ORGANIC CHEMISTRY (030500)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2013 CSIRO Publishing
Deposited On: 28 Jan 2014 04:36
Last Modified: 30 Jan 2014 23:41

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