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Improved One‐Pot Synthesis of Styryl Tetrahydrofurans and Cyclohexanes by Radical Addition to β ‐Nitrostyrenes in the Presence of Benzoyl Peroxide
Author(s) -
Jang YeongJiunn,
Shih YuhKuo,
Liu JingYuan,
Kuo WenYu,
Yao ChingFa
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200204571
Subject(s) - benzoyl peroxide , chemistry , cyclohexanes , radical initiator , selectivity , stereoselectivity , substrate (aquarium) , reactivity (psychology) , hydrogen peroxide , combinatorial chemistry , organic chemistry , catalysis , medicine , polymer , oceanography , alternative medicine , pathology , polymerization , geology
Stereoselective styryl derivatives have been prepared based on radical substitution (addition–elimination) of heterocycles or cyclohydrocarbons units to ( E ) ‐β ‐nitrostyrenes 1 using a common radical initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by using this easy methodology. The reactions using easily obtained and one‐pot potential starting materials gave excellent trans ‐selectivity with medium to high yields in all cases. Synthetic utility of this approach has been demonstrated by the preparation of various trans ‐styryl derivatives.