Tetrahedron Letters p. 2887 - 2890 (1992)
Update date:2022-09-26
Topics:
Feringa, Ben L.
Jager, Wolter F.
De Lange, Ben
The synthesis and resolution of 2-methyl-9H-thioxanthene-9-(9H-thioxanthen-9-ylidene) 1 and related structures 2-5, being the first examples of thermally stable optically active sterically overcrowded ethylenes, are reported. Substitution of the sulfur atom in the thioxanthene part of 1 with an X group (2, X = C(CH32; 3, NCH3 4, O) results in a change in racemization barrier (1, 27.4 kcal.mol-1; 3, 21.3 kcal.mol1 4, < 20 kcal.mol-1) depending upon the aryl-X bond lengths.
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