Volume 24, Issue 14
Preparative Organic Chemistry
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ChemInform Abstract: One-Step Spiroannulation Using 1,2-Bis(methylene)cycloalkane-Magnesium Reagents.

R. D. RIEKE

R. D. RIEKE

Dep. Chem., Univ. Nebraska, Lincoln, NE 68588-0304, USA

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H. XIONG

H. XIONG

Dep. Chem., Univ. Nebraska, Lincoln, NE 68588-0304, USA

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First published: April 6, 1993

Abstract

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ChemInform Abstract

Treatment of the 1,2-bis(methylene)cycloalkanes (I) with activated magnesium generates a 1,2-bis(methylene)cyclohexane magnesium complex which is quenched with the α,ω-dihaloalkanes (II) to yield the spirocyclic compounds (III). Furthermore, quenching with the . omega.-bromo nitriles (IV) followed by hydrolytic work-up gives the spirocyclic ketones (V).

chemical structure image

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