Organolithium compounds, 1,4-addition

Octynoic acid, methyl ester, 55, 76 ORGANOLITHIUM COMPOUNDS, addition to allyl alcohols, 55, 1... 

Organomagnesium compounds usually resemble organolithium compounds in their reactions with nitrogen heterocyclic aromatic compounds [E, G], but they generally give inferior results for preparative purposes. Thus, as in the case of organolithium compounds, addition normally occurs at the 2-position of pyridine, and subsequent elimination or oxidation gives the 2-substituted pyridine [1] ... 

Addition of Grignard reagents and organolithium compounds (Sections 14 6-14 7) Aldehydes are converted to secondary alcohols and ketones to tertiary alcohols... 

Addition of Grignard reagents and organolithium compounds to the pyridazine ring proceeds as a nucleophilic attack at one of the electron-deficient positions to give initially... 

Addition of phenylmagnesium bromide to phthalazin-l(2//)-one or derivatives like 4-phenylphthalazin-l(2/f)-one, 4-phenylphthalazine-l(2/f)-thione and 2-substituted phthalazin-l(2//)-ones results in the formation of 1,4-diphenylphthalazines, while addition of organolithium compounds to phthalazin-l(2/f)-one gives the 4-substituted derivative. 

RR C=NLi) . They can be prepared in high yield either by the addition of an organolithium compound across the triple bond of a nitrile (equation (1)) or by lithiation of a ketimine (equation (2)). 

As with the reduction of aldehydes and ketones (16-23), the addition of organometallic compounds to these substrates can be carried out enantioselectively and diastereoselectively. Chiral secondary alcohols have been obtained with high ee values by addition to aromatic aldehydes of Grignard and organolithium compounds in the presence of optically active amino alcohols as ligands. ... 

Good yields of phosphines have been obtained by the simultaneous addition of an organolithium compound and an alkyl chloride to a solution of a cyclopolyphosphane (6). 

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