2-Cyanomethylbenzaldehyde - useful substrate for preparation of some 1,3-di- and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo(2.2.2)octenes

doi:10.3998/ARK.5550190.0010.710

Paper

2-Cyanomethylbenzaldehyde - useful substrate for preparation of some 1,3-di- and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo(2.2.2)octenes

Published Apr 7, 2009 · M. Panasiewicz, T. Zdrojewski, Krzysztof Chrulski

Arkivoc

Q4 SJR score

3

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Abstract

Cyanomethylbenzaldehyde reacts in the presence of concentrated aqueous solution of sodium hydroxide or powdered potassium carbonate and a quaternary ammonium salt as a catalyst in benzene (phase-transfer catalysis) with 2-chloroethyl aryl ketones or electrophilic alkenes affording 1-cyano-3-acylnaphthalenes, 1-(2-cyano)- and 1-(2-phenylsulfonyl)ethyl-3-substituted naphthalenes or 1-cyano-5,8-diaroyl-benzobicyclo(2.2.2)octenes. Further cyclization of the corresponding 5,8-diacetyl derivative of 1-cyanobenzobicyclooctene gives 1-cyano-10- methyltetracyclo(7.5.1.0 2,7 .0 8,13 )pentadeca-2,4,6,10-tetraen-12-one. Formation of these products is rationalized.

Study Snapshot

2-Cyanomethylbenzaldehyde is a useful substrate for the preparation of 1,3-di- and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo(2.2.2)octenes, with potential applications in organic

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

2-Cyanomethylbenzaldehyde - useful substrate for preparation of some 1,3-di- and 1,2,3-trisubstituted naphthalenes or substituted 1-cyanobenzobicyclo(2.2.2)octenes

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