Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene

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Title:Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene
Creators:
Çakmak, Osman
Kahveci, Ismail
Demirtaş, Íbrahim
Hökelek, Tuncer
Smith, Keith
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 11, pp. 1791-1804
Uncontrolled Keywords:Photobromination, Bromination, Naphthalenes, Tetralin, Aromatic nucleophilic substitution, Halogenation, Bromine

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 (<strong>4</strong>) as a&nbsp;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 (<strong>10</strong>) gave 1,4-dibromonaphthalene (<strong>11</strong>) as the sole product in a high yield. 1,4-Dibromonaphthalene is efficiently converted to the corresponding methoxy (<strong>12</strong> and <strong>13</strong>) and cyano (<strong>14</strong> and <strong>15</strong>) derivatives of naphthalene. <p>

Title:Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene
Creators:
Çakmak, Osman
Kahveci, Ismail
Demirtaş, Íbrahim
Hökelek, Tuncer
Smith, Keith
Uncontrolled Keywords:Photobromination, Bromination, Naphthalenes, Tetralin, Aromatic nucleophilic substitution, Halogenation, Bromine
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:11
Page Range:pp. 1791-1804
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001791UNSPECIFIED
ID Code:1759
Item Type:Article
Deposited On:06 Feb 2009 17:12
Last Modified:06 Feb 2009 16:12

Citation

Çakmak, Osman; Kahveci, Ismail; Demirtaş, Íbrahim; Hökelek, Tuncer; Smith, Keith (2000) Bromination of Tetralin. Short and Efficient Synthesis of 1,4-Dibromonaphthalene. Collection of Czechoslovak Chemical Communications, 65 (11). pp. 1791-1804. ISSN 0010-0765

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