Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a
−
f and 5a
−
d, all
containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to
aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant
N-(β-hydroxyalkyl)benzotriazole derivatives 3a
−
m, 6a
−
g, 9a
−
d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a
−
m, dienes 7a
−
j, and triene
11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates.
This method offers an alternative to the three most frequently used methods for the formation of
alkenes from carbonyl compoundsthe Wittig, Peterson, and Julia reactionsespecially in the
formation of tri- and tetrasubstituted alkenes.
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