EFFECT OF PRESSURE ON THE CONROTATORY OPENING OF CYCLOBUTENES - AN UNEXPECTED RESULT

Authors
JENNER G
Citation
G. Jenner, EFFECT OF PRESSURE ON THE CONROTATORY OPENING OF CYCLOBUTENES - AN UNEXPECTED RESULT, Tetrahedron, 54(12), 1998, pp. 2771-2776
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
12
Year of publication
1998
Pages
2771 - 2776
Database
ISI
SICI code
0040-4020(1998)54:12<2771:EOPOTC>2.0.ZU;2-4
Abstract
Against intuitive expectation, conrotatory opening of cyclobutenes 1-4 is slightly promoted by pressure with activation volumes around -2 to -3 cm(3).mol(-1). The volume profile shows a minimum for the transiti on state TS. This result together with low activation entropy values d emonstrates full concertedness and suggest a cyclic TS with a preferen tial orbital topology. (C) 1998 Elsevier Science Ltd. All rights reser ved.