And Can Lead to Remarkable Rearrangements A Failed

Japanese workers recently designed a synthesis of 5-amino-2,3-dihydrothiepino[2,3- ]pyridine-4-carbonitrile 2 based on Thorpe-Ziegler cyclisation of 2-(3-cyanopropylthio)pyridine-3-carbonitrile 1. Treatment of 1 with potassium t-butoxide however, did not, give 2, but produced the thieno[2,3-/i][l,6]naphthyridine 3 in 82% yield. 

A Remarkably Stable Tertiary Alcohol by Solvolysis of a Primary 

The following is a typical example of a process described by Russian workers as anionic activation , and used for the rapid construction of fluoro-substituted heterocycles Treatment of 2-(trifluoromethyl)aniline with either lithium phenylacetylide or the lithium enolate of acetophenone in THF at -60°C gave 4-fluoro-2-phenylquinoline in 25-40% yield. 

Suggest a mechanism for this transformation and predict the structure of the product that would be formed if the same concept were applied to the condensation of 2-(trifluoromethyl)benzyl chloride with 2-benzo[h]thienyllithium. 

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