Triphenylmethyl reaction with atomic hydrogen

Treatment of 2/Z-chromenes which have at least one hydrogen atom at C-2 with acid gives a mixture of chroman and benzopyrylium salt (68T949). Reaction of a chromerte with triphenylmethyl salts gives essentially only the benzopyrylium salt (67AC(R)1045, 72CR(C)(274)650>. 

This conclusion had to be revised when Piehl and Brown showed that although they were able to repeat Haller s work on the alkylation of phenylcyclopropyl ketone (199) by means of sodium amide and methyl iodide to give 200 (a reaction which they thought was wrong), unexpected reactions occurred in the case of ethyl cyclopropanecarboxylate (201). With sodium amide the amide (202), and with triphenylmethyl sodium the ketone (203) is formed. The latter reaction is normally typical of esters having no a-hydrogen atom ... 

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