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Synthesis and Reactions of New Dithiolopyrroles
Author(s) -
Stachel HansDietrich,
Eckl Eduard,
ImmerzWinkler Elisabeth,
Kreiner Christine,
Weigand Wolfgang,
Robl Christian,
Wünsch Ralf,
Dick Stefan,
Drescher Norbert
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200290022
Subject(s) - chemistry , nucleophile , electrophile , ring (chemistry) , crystal structure , bicyclic molecule , oxidative addition , stereochemistry , medicinal chemistry , crystallography , catalysis , organic chemistry
The title compounds were prepared starting from pyrrolinone 4 . Nucleophilic‐displacement and ring‐closure reactions yielded the dithiolopyrrole 5a , which formed salts with electrophiles ( 7, 8 ) as well as with bases. The crystal structure of 5a was determined. Oxidation of the dithioles 5a and 6a led to S (2)‐oxides ( 10a, 11a ) and the corresponding S (2)‐dioxides ( 10b, 11b ) depending on reaction conditions. The thiosulfinate 10a was converted by a ring‐opening/ring‐closure reaction sequence to the bicyclic sulfinamide 12 . The oxidative addition reactions of [Pt( η 2 ‐C 2 H 4 ) (PPh 3 ) 2 ] ( 14 ) with the disulfides 5a and 13 led to the dithiolatoplatinum(II) complexes 15 and 16 , respectively. Complex 16 was characterized structurally. The sulfenato‐thiolato complex 17 was synthesized via reaction of 14 with the thiosulfinate 10a . The thiosulfonato Pt II complex 18 was prepared by an oxidative insertion of Pt 0 into the CS bond of the corresponding thiosulfonate 10b . Furthermore, complex 18 was characterized by single‐crystal X‐ray‐diffraction studies.