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Dithietanes. Synthesis of N ‐substituted 2‐imino‐1,3‐dithietanes and 2‐imino‐1,3‐dithietane hydrochloride
Author(s) -
Addor Roger W.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070221
Subject(s) - chemistry , hydrochloride , hydroxylamine hydrochloride , hydrochloric acid , salt (chemistry) , yield (engineering) , potassium , hydrolysis , medicinal chemistry , bromide , condensation , isothiocyanate , potassium bromide , organic chemistry , materials science , physics , metallurgy , thermodynamics
The reaction of diethylphosphoryl isothiocyanate with potassium hydrosulfide gave potassium diethoxyphosphinyldithiocarbamate ( 3a ). This salt, with methylene bromide, afforded 2‐diethoxyphosphinylimino‐1,3‐dithietane ( 5a ) in high yield. In concentrated hydrochloric acid, 5a was hydrolyzed to 2‐imino‐1,3‐dithietane which was isolated as a stable hydrochloride ( 7 ). The synthesis of some other N ‐Substituted 2‐imino‐1,3‐dithietanes is also described.