Product of an SN2' Ring-Opening Reaction, (1R*,2R*,3R*,4R*,7R*)-2,4,7-Trimethylcyclohept-5-ene-1,3-diol
Abstract
<h2>Acta Crystallographica Section C</h2><h3>Crystal Structure Communications</h3><h3>0108-2701</h3> <h2>organic compounds</h2> Volume 51 Part 5 Pages 912-914 May 1995 <h2>Product of an S N 2' Ring-Opening Reaction, (1 R *,2 R *,3 R *,4 R *,7 R *)-2,4,7-Trimethylcyclohept-5-ene-1,3-diol</h2> J. Colucci, C. Gajda, M. Lautens and A. J. Lough Product of an SN2' Ring-Opening Reaction, ( IR*,2R*,3R *,4R*, 7R * )- 2,4,7- T rime th yl- cyclohept-5-ene- 1,3-diol JOHN COLUCCI, CHRISTOPHER GAJDA, MARK LAUTENS AND ALAN J. LOUGH Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 1A1 (Received 5 August 1994; accepted 30 September 1994) Abstract The relative stereochemistry of the title compound, C10H1802, has been confirmed. The geometry of the seven-membered ring indicates that it is strained. Molecules are linked by O--H-..O hydrogen bonds [O...O 2.796 (3) and 2.816 (3),~,] about independent 71 inversion sites to form infinite columns with two inde- pendent (---O--H---O--H.. ")2 rings. Comment It has been shown that treatment of the [3.2.1]- oxabicyclic compound (1), 2,7-dimethyl-3,6-epoxy- cyclohept-4-enol, with excess methyllithium in TMEDA (N,N,N',N'-tetramethylethylenediamine) can promote a formal SN2~ ring-opening reaction to yield the cyclo- heptene compound (2) (Lautens, Abd-EI-Aziz & Lough, 1990). It was noted, however, that this ring opening could be accomplished only if