Is the magnetic shielding effect of a lactone group the simple sum of those of a ketone and an ether?

Authors
Fukazawa, Y Haino, T Kondoh, Y
Citation
Y. Fukazawa et al., Is the magnetic shielding effect of a lactone group the simple sum of those of a ketone and an ether?, TETRAHEDR L, 40(18), 1999, pp. 3591-3594
Citations number
28
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
18
Year of publication
1999
Pages
3591 - 3594
Database
ISI
SICI code
0040-4039(19990430)40:18<3591:ITMSEO>2.0.ZU;2-I
Abstract
3-Oxo-4-oxa-5 alpha-androstanone (1) was synthesized in order to obtain the NMR shielding parameters for lactone group. The assignment of H-1-NMR and substituent-induced shifts (SIS) from the corresponding androstanone (2) ar e presented. A simple sum of the magnetic shieldings of ketone and ether ca n satisfactorily reproduce the observed SIS values due to the lactone group of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.