Journal of the Chemical Society. Perkin transactions I p. 2209 - 2212 (1988)
Update date:2022-08-05
Topics:
Birkinshaw, Timothy N.
Meakins, G. Denis
Plackett, Simon J.
The conformational preferences of 2-(N,N-disubstituted amino)thiazoles having a 4-substituent (R1) and a 5-acyl group (R2CO) have been established by i.r. spectrometry and a crystallographic examination.In solution the compounds with R2=aryl and R1=Me or aryl exist predominantly or entirely in the carbonyl O,S-anti arrengement; for those with R1=aryl and R2=Me the syn rotamer is the main form but a small amount (ca. 15percent) of the anti rotamer is present.Nitrosation of 4-aryl-2-dimethylaminothiazoles gives 5-nitoso derivatives, and these are probably the first authentic nitrosothiazoles.The barrier to rotation of the dimethylamino group is unexpectedly high (ΔG(excit.)298=69 kJ mol-1), exceeding even that of the 5-trifluoroacetyl analogous.
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