90145-07-6Relevant academic research and scientific papers
Condensed Ring Systems, XV. About the Reaction of α-Chloro Sulfoxides with Potassium tert-Butoxide by the Example of the Synthesis of Oxapropellenes
Weinges, Klaus,Kasel, Wolfgang,Klein, Juergen,Hubertus, Georg,Irngartinger, Hermann,et al.
, p. 966 - 981 (2007/10/02)
The synthesis of dithia- 1a-3a and oxathiapropellenes 1b-3b is described.From 1b-3b the α-chloro sulfoxides 4-6 and α-chloro sulfones 4a-6a are prepared, of which in most cases several stereoisomeric racemates are obtained.The constitution, configuration, and conformation of the α-chloro sulfoxide 4, the main product obtained from 1b, was elucidated by X-ray structure analysis.Only in that way it was possible to deduce the constitutions and configurations of the other stereoisomeric α-chloro sulfoxides 4-6 and α-chloro sulfones 4a-6a, respectively, using 13C NMRspectroscopy.By the reaction of the α-chloro sulfones 4a-6a with potassium tert-butoxide (Ramberg-Baecklund reaction) the corresponding oxapropellenes 7-9 are obtained only in the low yields (10 percent).Contrary, the α-chloro sulfoxides 4-6 under analogous conditions give yields of 80 - 90 percent (from 4, 6) and 25 percent (from 5).
