Journal of the Chemical Society. Perkin transactions I p. 2338 - 2345 (1980)
Update date:2022-08-05
Topics:
Pover, Keith A.
Scheinmann, Feodor
The regioselectivity of the reactions of 1,3-dilithioalk-1-ynes with various electrophiles has been examined.With formaldehyde and cyclic ketones, reaction occur at C-1 and C-3 to give alk-2-yne-1,5-diols.In contrast reactions with carbon dioxide give allene-1,3-dicarboxylic acids. 1,3-Dilithioalk-1-ynes decompose hexamethylphosphoric triamide and the resulting N-methylmethyleneamine undergoes addition only at the propargylic site.Further reaction with either 1-bromobutane or water gives alkynylamines.Benzylideneaniline also reacts with 1,3-dilithiohex- and hept-1-ynes only at the propargylic site to give N-phenylbut-3-ynylamines.
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Doi:10.1016/S0040-4039(01)91879-9
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