Volume 19, Issue 4
Preparative Organic Chemistry
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ChemInform Abstract: A Facile Synthesis of 1,5-Dienes and β,γ-Unsaturated Nitriles via Trityl Perchlorate-Catalyzed Allylation.

M. MURAKAMI

M. MURAKAMI

Dep. Chem., Fac. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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T. KATO

T. KATO

Dep. Chem., Fac. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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T. MUKAIYAMA

T. MUKAIYAMA

Dep. Chem., Fac. Sci., Univ. Tokyo, Hongo, Tokyo 113, Japan

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First published: January 26, 1988

Abstract

The allyl ethers (Ib) - (Id), which are prepared from the alcohol (Ia), react with trimethylallylsilane (II) in the presence of trityl perchlorate as a catalyst to give the 1,5-dienes (IV) and (V).

ChemInform Abstract

The allyl ethers (Ib) - (Id), which are prepared from the alcohol (Ia), react with trimethylallylsilane (II) in the presence of trityl perchlorate as a catalyst to give the 1,5-dienes (IV) and (V). Trimethylsilyl cyanide (VI) and compounds (Ib) - (Id) produce the unsaturated nitrile (VII) analogously. The allylic ether (IX) and the acetals (VIII) and (X) react with the silanes (XI) - (XIII) in thesame manner, forming the corresponding substitution products. Further transformations in this series are described in the original paper.

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