Volume 21, Issue 1
Heterocyclic Compounds
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ChemInform Abstract: Lewis Acid-Mediated Nucleophilic Substitution Reactions of 2-Alkoxy-3,4-dihydro-2H-1-benzopyrans: Regiochemistry and Utility in the Synthesis of 3,4-Dihydro-2H-1-benzopyran-2-carboxylic Acids.

N. COHEN

N. COHEN

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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B. SCHAER

B. SCHAER

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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G. SAUCY

G. SAUCY

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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R. BORER

R. BORER

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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L. TODARO

L. TODARO

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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A.-M. CHIU

A.-M. CHIU

Roche Res. Cent., Hoffmann-La Roche Inc., Nutley, NJ 07110, USA

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First published: January 2, 1990

Abstract

The reaction of the chromans (I) and (VI) with the cyanosilanes (II) is catalyzed by Lewis acids to yield the corresponding nitriles (III) and (VII).

ChemInform Abstract

The reaction of the chromans (I) and (VI) with the cyanosilanes (II) is catalyzed by Lewis acids to yield the corresponding nitriles (III) and (VII). The chroman (Ic) also reacts with the nucleophiles (IV), forming the substitution products (V). Reaction of the spiroacetal (VIII) with the cyanosilane (II) leads to the formation of the nitriles (IX) or (XI) depending on the kind of Lewis acid employed as the catalyst.

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