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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 22
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Original Articles

Claisen and Fries Rearrangement Studies of Some Naphthalene Derivatives

Ivan R. Green Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville, 7530, Republic of South Africa
,
Shawlene Nefdt Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville, 7530, Republic of South Africa
,
Victor I. Hugo Department of Chemistry, Cape Technikon, P.O. Box 652, Cape Town, 8001, Republic of South Africa
&
Petra W. Snijman Department of Chemistry, Cape Technikon, P.O. Box 652, Cape Town, 8001, Republic of South Africa
Pages 3189-3196 | Received 22 Apr 1994, Published online: 23 Sep 2006
 
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Abstract

Comparative Claisen rearrangements of 4-hydroxy - (7) and 4-acetoxy-1-allyloxy-5,8-ethano-5,8-dihydro-5-methoxynaphthalene (1) leading after chemoselective methylation to 4-acetoxy-2-allyl-1,5-dimethoxy-naphthalene (9) were investigated. Lewis acid mediated Fries rearrangements of 4-acetoxy-2-allyl-alkoxy-5-ethoxynaphthalenes lead to the formation of a naphtho[1,2 - b]furan in one case only.

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