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Selective production of 1-arylalkenes : Synthesis of 1-aryl-2-alkenes and 1-arylalkanes via Friedel-Crafts alkylation of aromatic substrates with allylic alcohols over solid acid catalysts

Smith, Keith, Pollaud, Guy M. and Matthews, Ian 1999. Selective production of 1-arylalkenes : Synthesis of 1-aryl-2-alkenes and 1-arylalkanes via Friedel-Crafts alkylation of aromatic substrates with allylic alcohols over solid acid catalysts. Green Chemistry 1 (2) , pp. 75-81. 10.1039/A901394F

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Abstract

Moderately activated benzenoid compounds undergo alkylation with allylic chlorides and particularly allylic alcohols over solid acid catalysts. Acidic K10 clay is the optimal catalyst and allows almost exclusive attack at the terminal position of the intermediate allyl cation to yield 1-aryl-2-alkenes. Catalytic hydrogenation quantitatively yields the corresponding 1-arylalkanes. Phenol also reacts readily but gives a significant quantity (ca. 12%) of 3-aryl-1-butene along with 1-aryl-2-butene.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1463-9262
Last Modified: 04 Jun 2017 02:51
URI: http://orca.cf.ac.uk/id/eprint/12735

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