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Cover Picture: Formation of Triazinium‐Imidothioate Zwitterions and Their Role as Key Intermediates for Novel S N (ANRORC) Reaction Pathways (Eur. J. Org. Chem. 8/2003)
Author(s) -
Wermann Kurt,
Walther Martin,
Günther Wolfgang,
Görls Helmar,
Anders Ernst
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390207
Subject(s) - chemistry , deprotonation , zwitterion , intramolecular force , amine gas treating , reactive intermediate , reaction mechanism , stereochemistry , bicyclic molecule , rearrangement reaction , medicinal chemistry , computational chemistry , molecule , organic chemistry , catalysis , ion
The cover picture shows a calculated [DFT‐(B3LYP/6‐311++G(d,p) level] “standardized” structure of the title compounds, the highly reactive triazinium‐imidothioates (center). These are readily accessible by the reaction of an amine with a bis(thiadiazolo)‐triazinium salt which is followed by deprotonation (top) and a spontaneous ring opening step. These zwitterions stabilize themselves by intramolecular cyclization reactions under the formation of either highly substituted guanidines (left) or triazolo‐thiadiazolo‐triazinium (center) or bis(triazolo)‐triazinium cations (right). Important reaction steps are initiated by negative hyperconjugation which controls the reaction modes of key intermediates. Experimental and theoretical details are discussed in the article by E. Anders et al. on p. 1389 ff.