Synlett 2005(1): 184-185  
DOI: 10.1055/s-2004-837196
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Mesityllithium

Santosh Baburao Mhaske*
Division of Organic Chemistry (Synthesis), National Chemical ­Laboratory, Pune - 411 008, Maharashtra, India
Fax: +91(20)25893153; e-Mail: msantosh@dalton.ncl.res.in;
Further Information

Publication History

Publication Date:
07 December 2004 (online)

Introduction

The use of lithium reagents in organic synthesis is well documented in the literature. [1-3] Amongst the other reagents, mesityllithium has occupied an important place [4-24] because of its non-nucleophilicity, strongly basic nature, clean selective reactivity and easy preparative methods. 2-Bromomesitylene is treated with tert-butyllithium in THF solution, a method that leads to a 1:1 mixture of the reagent and lithium bromide (Scheme 1). [4] [11] [12] For large scale reactions, it may be more convenient to prepare mesityllithium from bromomesitylene and lithium metal. [13-15]

Scheme 1 Preparation of mesityllithium reagent

The highly hindered mesityllithium reagent is monomeric [16] i.e. not aggregated as are most other lithium derivatives. Freshly prepared mesityllithium is normally used, but mesityllithium may be stored, refrigerated, in solution with Et2O/THF under Ar or N2.

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