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Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene

Cakmak, Osman, Kahveci, Ismail, Demirtas, Ibrahim, Hokelek, Tuncer and Smith, Keith 2000. Bromination of tetralin. Short and efficient synthesis of 1,4-dibromonaphthalene. Collection of Czechoslovak chemical communications 65 (11) , pp. 1791-1804. 10.1135/cccc20001791

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Abstract

High-temperature bromination of tetralin (1,2,3,4-tetrahydronaphthalene) with bromine resulted in benzylic bromination to give 1,4-dibromo-1,2,3,4-tetrahydronaphthalene (4) as a major product and several secondary products. Photolytic bromination of tetralin and subsequent double dehydrobromination of 1,1,4,4-tetrabromo-1,2,3,4-tetrahydronaphthalene (10) gave 1,4-dibromonaphthalene (11) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (12 and 13) and cyano (14 and 15) derivatives of naphthalene.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Bromine; Photobromination; Bromination; Halogenation; Naphthalenes; Tetralin; Aromatic nucleophilic substitution
Publisher: Institute of Organic Chemistry and Biochemistry
ISSN: 0010-0765
Last Modified: 04 Jun 2017 02:57
URI: http://orca.cf.ac.uk/id/eprint/14288

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