Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes

Authors
Mori, H Matsuo, T Yoshioka, Y Katsumura, S
Citation
H. Mori et al., Vinyl hydrogen more reactive than benzyl hydrogen toward base in significantly twisted styrenes, TETRAHEDR L, 42(17), 2001, pp. 3093-3095
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
17
Year of publication
2001
Pages
3093 - 3095
Database
ISI
SICI code
0040-4039(20010423)42:17<3093:VHMRTB>2.0.ZU;2-C
Abstract
The novel example of vinyl hydrogen more reactive than benzylic hydrogen wa s found by treatment of a twisted styrene derivative with a strong base fol lowed by D2O quenching. The characteristic nature of the vinyl hydrogen, wh ich is activated by sigma-pi* orbital interaction, was apparently demonstra ted. (C) 2001 Elsevier Science Ltd. All rights reserved.