Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and beta-nitrostyrenes

Authors
Liu, JY Liu, JT Yao, CF
Citation
Jy. Liu et al., Novel synthesis of alkenes via triethylaluminum-induced free radical reactions of alkyl iodides and beta-nitrostyrenes, TETRAHEDR L, 42(21), 2001, pp. 3613-3615
Citations number
40
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
21
Year of publication
2001
Pages
3613 - 3615
Database
ISI
SICI code
0040-4039(20010521)42:21<3613:NSOAVT>2.0.ZU;2-I
Abstract
Reactions of (E)-beta -nitrostyrenes 1 with triethylaluminum (Et3Al) 2 and alkyl iodide (RI) 3, 4, or 5 in the presence of benzoyl peroxide in diethyl ether solution at room temperature to give 60-100% of the different (E)-al kenes 6, 7, or 8. Under similar conditions, 95% of 1-adamantyl-2-(4-methoxy phenyl)ethene 10 or 80% of 1-(4-oxoadamantyl)-2-(4-methoxyphenyl)ethene 12 also can be easily prepared by using 1-iodoadamantane 9 or 5-iodo-2-adamant anone 11 and 2. (C) 2001 Elsevier Science Ltd. All rights reserved.