Infoscience

Journal article

Hetero-atom effects on kinetic acidities: the metalation of 1-methylcyclohexene and its 4-aza- and 4-oxa-analogs

Hexane suspensions of Me3SiCH2K or BuLi/Me3COK deprotonated 1-methylcyclohexene almost exclusively at the Me group. In contrast 1,4-dimethyl-1,2,3,6-tetrahydropyridine and 4-methyl-5,6-dihydro-2H-pyran preferentially underwent H/metal-exchange at the N-distant and oxygen-adjacent allylic methylene groups, resp. Strong amide bases converted 5,6-dihydro-2H-pyrans into (Z)-pentadienols. The mechanism of the latter ring-opening is discussed. [on SciFinder (R)]

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