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1,3‐Dithiole mit anelliertem Cyclopentadienring
Author(s) -
Hartke Klaus,
Timpe Carsten
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940212
Subject(s) - chemistry , iminium , cyclopentadiene , pyrrolidine , yield (engineering) , acetone , ring (chemistry) , medicinal chemistry , sodium , organic chemistry , polymer chemistry , catalysis , materials science , metallurgy
1,3‐Dithiols with an Annulated Cyclopentadiene Ring 5‐Chloro‐2‐cyclopenten‐1‐ones 4 react with sodium N, N ‐di‐alkyldithiocarbamates to form the dithiocarbamic esters 5 . These are cyclized by strong acids to yield either in a Michael addition the iminium salts 6 or in a condensation reaction the iminium salts 7 . Sulfhydrolysis of 7 gives rise to the 4 H ‐cyclopenta‐1,3‐dithiol‐2‐thione 8 . By cleavage of dithiuram disulfides 10 with sodium cyclopentadienide the [(dial‐kylamino)thiocarbonylthio]cyclopentadienes 12 and 13 are formed. They condense with acetone/pyrrolidine to give either the pentafulyenes 16 or the dihydropentalenes 17 .