Base-induced photorearrangements from 3-styrylfurans to 2-methylnaphthalenes
摘要:
Irradiation of 3-(4-substituted styryl)furans in basic media yielded a series of 7-substituted-2-methylnaphthalenes, including methoxy, isopropyl, ethyl, methyl, fluoro, and cyano substituents. This base-induced photorearrangement involves cis-trans photoisomerization, 6e photocyclization, base-induced elimination, and a Norrish Type I photoreaction and is a novel method to synthesize unsymmetrical 2,7-disubstituted naphthalenes. (C) 2011 Elsevier Ltd. All rights reserved.
Construction of polyaromatics via photocyclization of 2-(fur-3-yl)ethenylarenes, using a 3-furyl group as an isopropenyl equivalent synthon
作者:Ying-Zhe Chen、Ching-Wen Ni、Fu-Lin Teng、Yi-Shun Ding、Tunng-Hsien Lee、Jinn-Hsuan Ho
DOI:10.1016/j.tet.2014.01.035
日期:2014.3
The construction of different types of substituted arenes was demonstrated through the photocyclization of 2-(fur-3-yl)ethenylarenes using a 3-furyl group as an isopropenyl equivalent synthon in the photocyclization reaction. The furan portion of the photocyclization intermediate could be fragmented via a base-induced elimination reaction to yield a series of substituted polyaromatics, including naphthalene
Regioselective synthesis of substituted 1-methyl- and 2-methylnaphthalenes
作者:K Mallik Yadav、Pramod K Mohanta、Hiriyakkanavar Ila、Hiriyakkanavar Junjappa
DOI:10.1016/0040-4020(96)80832-5
日期:1996.10
Regiospecificallysubstituted 1-methyl- and 2-methylnaphthalenes, 5-methyl- and 6-methyl-1,2,3,4-tetrahydroanthracenes have been synthesized in good yields through 1,2- addition of the corresponding α-lithio-o-or m-xylenes onto α-oxoketenedithioacetals or their dihydro derivatives followed by cyclodehydration of the resulting carbinols in the presence of borontrifluoride etherate.