Chemistry of Heterocyclic Compounds: Thiophene and its by Salo Gronowitz
By Salo Gronowitz
Chapter I coaching of Thiophenes by means of Ring?Closure Reactions and from different Ring platforms (pages 1–214): Salo Gronowitz
Chapter II Theoretical Calculations on Thiophenes (pages 215–260): Anita Henriksson?Enflo
Chapter III evidently Occuring Thiophenes (pages 261–324): F. Bohlmann and C. Zdero
Chapter IV Thiophenes happening in Petroleum, Shale Oil, and Coals (pages 325–352): G. D. Galpern
Chapter V Pharmacologically lively Compounds and different Thiophene Derivatives (pages 353–456): Jeffery B. Press
Chapter VI relief and Desulfurization of Thiophene Compounds (pages 457–570): L. I. Belen'Kii and Y. A. L. Gol'Dfarb
Chapter VII Thiophene 1,1?Dioxides, Sesquioxides, and 1?Oxides (pages 571–628): Maynard S. Raasch
Chapter VIII response at Sulphur (pages 629–650): A. E. A. Porter
Chapter IX Radical Reactions of Thiophene (pages 651–670): A. E. A. Porter
Chapter X Cycloaddition Reactions of Thiophenes, Thiophene 1?Oxides, and 1,1?Dioxides (pages 671–744): P. H. Benders, D. N. Reinhoudt and W. P. Trompenaars
Chapter XI Photochemical Reactions of Thiophenes (pages 745–770): Alain Lablache?Combier
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Additional info for Chemistry of Heterocyclic Compounds: Thiophene and its Derivatives, Part One, Volume 44
The a,b-unsaturated nitrile 147 is first prepared by a Knoevenagel-Cope condensation and then reacted with sulfur and amine. Examples of the two-step procedure are given in Table 19. NEO] [ - CH, CONHPh I(CH,),SCH, 1 (CH,), --[(CH2) ,N(CH,)CH, 1CH-(CH,), R2 R24Hz R,--CO + CN A cisltrans 5,7-Me, mixture. (70) Yield of Thiophene CN CN CN CN CN CN CN CN CN CN CN CN CN CN 45 44 86 goa 74 80b 64 43 17 18 60 68 79 63 50 5 CN S 42 70 61 86 62 t CN CN CN CN CN X CHzX I THE GEWALD REACTION - MODIFICATION 2 a Another structure for these compounds is given in the publication.
17' Both 2-13C-and 3-13Cenriched thiophenes have been prepared by this method from, appropriately, 13C-enriched sodium ~ u c c i n a t e . ' ~A~ detailed procedure for the synthesis of 3-methylthiophene in 52-60% yield from disodium methylsuccinate, using mineral oil as diluent, has also been p~blished,'~'and 3-ethylthiophene was similarly and 3-aobtained from disodium e t h y l s u ~ c i n a t e . '41 In connection with work on optically active (+)-S-3-sec. butylthiophene, the reaction of optically active sec.
Similarly, the furanothiophenophane 112 was prepared from 1 1 1203 (Scheme 47). Mixed sulfides, such as 113, have also O + H Nc/ I - c // H\ 0 109 Yield (%) n 3 4 5 (CH30H) 6 (CH30H) 7 8 (CH30H) 10 110 9 36 3 4 (42) 44 ( 6 1 ) 61 58 (73) 91 (95) Scheme 46 111 112 Scheme 47 been used in the reaction with glyoxal, phenyl glyoxal, a-diketones, glyoxylates, mesaoxalates, and oxalates to give di- and trisubstituted thiophenes. '~~-~~~~'~~ metrical a-dicarbonyl compounds leads regiospecifically to only one isomer.