✦ LIBER ✦

On the stability of 3-benzo[b]thienyl-lithium

✍ Scribed by R.P. Dickinson; B. Iddon

Book ID: 104248741
Publisher: Elsevier Science
Year: 1970
Tongue: French
Weight: 183 KB
Volume: 11
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)97882-7

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✦ Synopsis

Recently we' reported the synthesis and some reactions of 3-benzo [hJthienyllithium (I). When an ethereal solution of (I) was treated at -70" tuccessively with carbon dioxide and acid or with dimethyl sulphate, it gave high yields of benzo[h]thiol,hen-3-carboxylic acid and 3-methylbenzo[~]thiophen,reapectively. A similarly prepared solution of (I) stirred at 20" for 30 min. prior to carbonation gave benso[&~thiophen-2-carboxylic acid and 3-bromobenso[athiophen-2-carboxylic acid as the major products together with a trace of benso[_Q]thiophen-3-carboxylic acid. At that time we believed' that the behaviour of (L) in ether paralleled the reported2 behaviour of 3-thienyl-lithium in ether and, consequently, that reactions (l)+(3) were predominantly responsible for the formation of the above mixture of acids. + n-BuLi d OJ 1 I s ? + (1) d + n-BuBr (t)

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