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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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