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@article{635374,
author = {Čmelík, Richard and Pazdera, Pavel},
article_number = {5},
keywords = {1;2-Dithiole-3-thiones; Sulfur heterocycles; Trithiapentalenes; Rearrangements; X-ray diffraction; Reaction mechanism; Heterocyclizations.},
language = {eng},
issn = {0010-0765},
journal = {Collection of Czechoslovak Chemical Communications},
title = {TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES},
volume = {71},
year = {2006}
}
TY - JOUR
ID - 635374
AU - Čmelík, Richard - Pazdera, Pavel
PY - 2006
TI - TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES
JF - Collection of Czechoslovak Chemical Communications
VL - 71
IS - 5
SP - 650-666
EP - 650-666
SN - 00100765
KW - 1;2-Dithiole-3-thiones
KW - Sulfur heterocycles
KW - Trithiapentalenes
KW - Rearrangements
KW - X-ray diffraction
KW - Reaction mechanism
KW - Heterocyclizations.
N2 - We report the reactions of derivatives of 5-amino-3-thioxo-3H-1,2-dithiole-4-carboxylic acid 1 with bromoethanones and acylation agents. Two different routes were used to obtain the products, 3-(acylmethylidene)-3H-1,2-dithioles 4. These compounds were synthesized by acylation of compounds 1 on the amino group, followed by the reaction with bromoethanones and excess of triethylamine. Another method was based on the inverted order of the mentioned reaction steps and in absence of a base. The treatment of 4 with thionyl chloride gave new unsaturated fused lactones 13 whereas thionation led to desired 1,6,6alambda4-trithiapentalenes 5. The structures of products and the reaction mechanisms are discussed.
ER -
ČMELÍK, Richard a Pavel PAZDERA. TRANSFORMATION OF 1,2-DITHIOLE-3-THIONES INTO 1,6,6alambda4-TRITHIAPENTALENES via REACTION WITH BROMOETHANONES. \textit{Collection of Czechoslovak Chemical Communications}. 2006, roč.~71, č.~5, s.~650-666. ISSN~0010-0765.
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