Unexpected Formation of Bicyclic Cyclopropane Lactam and Pyridone from the Reaction of cis‐2‐Aryl‐1‐carbomethoxy‐3,3‐dicynocyclopropane with Primary Aliphatic Amine via Isomerization and Rearrangement

2006 ◽  
Vol 36 (17) ◽  
pp. 2441-2452 ◽  
Author(s):  
Zhongjiao Ren ◽  
Weiguo Cao ◽  
Sihui Wang ◽  
Yun Wang ◽  
Yeying Lu
Polymer ◽  
1980 ◽  
Vol 21 (10) ◽  
pp. 1167-1170 ◽  
Author(s):  
Victoria Wright ◽  
Geoffrey McGarraugh ◽  
Roger Phillips

1971 ◽  
Vol 36 (13) ◽  
pp. 1841-1842 ◽  
Author(s):  
Edward R. Biehl ◽  
Susan M. Smith ◽  
P. C. Reeves

2017 ◽  
Vol 13 ◽  
pp. 2502-2508 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Martin Dračínský ◽  
Petr Beier

A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni’s reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C–N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.


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