Unsaturated chlorohydrins (1) (readily obtained from crotonaldehyde) are converted, by methylation and in situ lithiation at room temperature, into alka-2,3-dienes (2).
REACTIONS OF 3-ALKYL- AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES: EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIO- AND STEREOSELECTIVITY
Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons.The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.
Caporusso, Anna Maria,Polizzi, Carmela,Lardicci, Luciano
p. 6073 - 6076
(2007/10/02)
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