ISSN:
1042-7163
Schlagwort(e):
Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Stereospecific ring openings of optically active 2,3-epoxy alcohols were performed by the reaction of 1, 3, 5, and 7 with carbon disulfide and sodium hydride to give the five-membered xanthates 2, 4, 6, and 8. Both enantiomers of 2-mercapto-1,3-diol triacetates, 11 and 14, were derived from 4 and 6, respectively. The ring opening reaction proceeded at -78°C to -30°C, and the yields were around 80%. However, at a higher temperature between 0°C to room temperature, a complicated reaction took place and led to the formation of two isomers of the cyclic thiol carbonates 15 and 16 from 1 or 5. These processes were also stereospecific, and mechanisms have been proposed. In the case of the 3,4-epoxy alcohol 20, the epoxide ring opening gave the six-membered xanthate 21 stereospecifically.
Zusätzliches Material:
1 Ill.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hc.520050110
Permalink