ISSN:
0749-1581
Keywords:
Dibenzodithiocins
;
Synthesis
;
1H and 13C NMR
;
Conformation
;
Structural isomerism
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-(3,4-Dialkoxyphenylthiomethyl)aroylamides (la, b) reacted with phosphoryl chloride to give not only the expected 4H- and 2H-1,3-benzothiazine derivatives (4a, b and 5a, b), but also dibenzodithiocins of new (dibenzo[d,g][1,3]dithiocins 2a, b) and known (dibenzo[b,f][1,5]dithiocins 3a, b) types. The analogous reaction of the 4-methylaroylamide 8a furnished the 4H-1,3-benzothiazine 9a, the dibenzo[b, f][1,5]dithiocin derivative 10a and benzonitrile. In contrast, 8b (the chloro analogue of 8a) furnished only benzonitrile and bis(4-chlorophenylmercapto)methane (11). The structures of the new compounds were confirmed by IR, 1H and 13C NMR, and (in part) by mass spectrometry. Temperature-dependent 1H NMR studies were used for the conformational analysis of 2a and its disulphone 6a; the nature and free enthalpies of activation of the two different conformational motions occurring at higher temperatures were determined.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260270809
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