Stereochemistry of 11-hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0((3,7))]undecan-9-one and related diols

Authors
Patel, AV Alexandropoulou, I Crabb, TA
Citation
Av. Patel et al., Stereochemistry of 11-hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0((3,7))]undecan-9-one and related diols, TETRAHEDRON, 56(51), 2000, pp. 10005-10009
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
51
Year of publication
2000
Pages
10005 - 10009
Database
ISI
SICI code
0040-4020(200012)56:51<10005:SO1>2.0.ZU;2-K
Abstract
11-Hydroxy-1,3,5,7,11-pentamethyl-2,4,6,8-tetraoxatricyclo[3.3.3.0((3.7))]u ndecan-9-one adopts an equilibrium (in CD2CI2 at -90 degreesC) between ca. 68% of the conformer with a pseudo-axial C-11 methyl substituent and ca. 32 % of the alternative pseudo-equatorially substituted conformer. The derived cis-9,11-diol, cis-9,11-dimethyldiol and cis-9-phenyl-11-methyldiol adopt conformational equilibria heavily biased towards the diaxial OH conformatio ns which are stabilised by internal H-bonds involving the dioxolan ring oxy gen atoms. (C) 2000 Published by Elsevier Science Ltd.