Synthesis and photochemistry of styryl substituted annelated furan derivatives. IV. Concentration directed intra- and/or intermolecular [2+2] cycloaddition

Škorić, Irena; Marinić, Željko; Sindler-Kulyk, Marija (2004) Synthesis and photochemistry of styryl substituted annelated furan derivatives. IV. Concentration directed intra- and/or intermolecular [2+2] cycloaddition. Croatica Chemica Acta, 77 (1-2). pp. 161-166. ISSN 0011-1643

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Abstract

New cyclobutane derivatives have been synthesized by intermolecular photochemical [2+2] ethene-ethene "head-to-head" (9a,b) and "head-to-tail" (10a,b-11a,b) as well as [2+2] ethene-furan (12a,b) cycloaddition from 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (2a) and 2-[2-(2-methylphenyl)ethenyl]benzo[b]furan (2b), respectively. All compounds were isolated and characterized by spectroscopic methods. Under the benzene solution irradiation of 5 x 10(-1) 1 mol dm(-3) concentration and higher, 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (2a) gave only dimeric products (9a-12a). At the 1 x 10(-1) mol dm(-3) concentration, a mixture of dimers (9a-12a) and 7,12-dihydro-7,12-methano-6H-benzo[4,5]cyclohepta[ 1,2-b]benzofuran (5) was formed in a ratio 2:1.

Item Type:	Article
Uncontrolled Keywords:	synthesis; photochemistry; furan; cyclobutane; benzo[b]furan; cycloaddition; ortho-divinylbenzenes; stereochemistry; NMR
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	NMR Center
Projects:	Project title Project leader Project code Project type Sintetska, fotokemijska i strukturna istraživanja heterocikličkih spojeva Marija Šindler 0125004 MZOS Nuklearna magnetska rezonancija i proračuni bioorganskih molekula Dražen Vikić-Topić 0098059 MZOS
Depositing User:	Željko Marinić
Date Deposited:	13 Nov 2013 14:12
URI:	http://fulir.irb.hr/id/eprint/936

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