Homologation of Halides

CF3C02H LiBr, NOBF4 NaBr, NaN02, H2S04 KBr, NaN02, H2SQ4 

NaN02 / KI, Cu KI, H2S04 / NaN02 / Cu AmONO, I2 AmONO, CH2I2 

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The two schemes showing homologation of halides through alkylation of phenylthiomethyllithium as the key step for carbon-carbon bond formation illustrate the potential of this reagent [303],... 

This homologation of an oxime ether may have wider application for coupling of alkyl halides to other substrates such as acrylic esters (equation II). 

Since alkyl phenyl teUurides are easily prepared from alkyl hahdes and phenyltel-luromethyllithium, procedure C constitutes a homologation of alkyl halides. 

In 1990, Hahn and Tompkins reported an interesting multi-carbon homologation of alkyl halides by the reaction of magnesium carbenoid with a Grignard reagent (Scheme 2) . 

Benzodiazocines have attracted much interest as homologs of 1,4-benzodiazepine drugs, and several efficient cyclization methods have been developed. The diamine (289 R = H), available by several routes from the aminobenzophenone, cyclizes slowly in hot pyridine, but treatment of the halide (288) with ammonia leads directly to (292), perhaps by prior... 

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