Volume 18, Issue 35
Organoelement Compounds
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ChemInform Abstract: Stoichiometric Generation of 3-Siloxyallenyllithium and Its Reactions with Electrophiles.

R. MATSUOKA

R. MATSUOKA

Dep. Chem., Fac. Sci., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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Y. HORIGUCHI

Y. HORIGUCHI

Dep. Chem., Fac. Sci., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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I. KUWAJIMA

I. KUWAJIMA

Dep. Chem., Fac. Sci., Tokyo Inst. Technol., Meguro, Tokyo 152, Japan

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First published: September 1, 1987

Abstract

The propargylic alcohol (I) reacts with butyllithium to give the allene (II) which is further lithiated and then substituted with the halides (IV), yielding the allenyl silyl ethers (V).

ChemInform Abstract

The propargylic alcohol (I) reacts with butyllithium to give the allene (II) which is further lithiated and then substituted with the halides (IV), yielding the allenyl silyl ethers (V). Hydrolysis gives the unsaturated ketones (VI). The lithium derivative (III) reacts with benzaldehyde (VII), forming the siloxyalkynylcarbinol (VIII). The unsaturated (cyclic) ketones (X) and (III) produce the allenyl ketones (XI) and the diketones (XII) in the presence of the copper acetylide (IX).

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