By Salo Gronowitz
Vinylthiophenes and Thienylacetylenes (S. Gronowitz & A.-B.
Organometallic Derivatives of Thiophenes (T. Frejd).
Syntheses, Reactions, and actual homes of Bithienyls and Polythienyls and heavily similar Compounds (R. H?kansson).
Chapter I Vinylthiophenes and Thienylacetylenes (pages 1–256): Salo Gronowitz and Anna?Britta Hornfeldt
Chapter II Organometallic Derivatives of Thiophenes (pages 257–754): Torbjorn Frejd
Chapter III Syntheses, Reactions, and actual homes of Bithienyls and Polythienyls and heavily comparable Compounds (pages 755–905): Rolf Hakansson
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Extra resources for Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Five, Volume 44
Same ~ ylide, generated with butyllithium in THF, was 44 Vinylthiophenes and Thienylacetylenes 206 208 207 reacted with 2,3-diformylthiophene, in which the 3-formyl group was protected as ethylene acetal, to give 210. which was used as an intermediate for the synthesis of t h i e n ~ p y r i d i n e s . 335 In connection with synthetic approaches to complex antitumor agents, a cis-trans mixture of 214 was prepared from the pyrrol-2-yl-methylphosphoniumiodide and 2-thiophene aldehyde, and the mixture was photochemically ring-closed to a thieno i n d ~ l e .
Preparation of Vinylthiophenes 175 QCH=CH 39 176 C H ;(C, H 177 )3 OHC ()CH(OC2Hs)2 178 Using 2 mol of the aldehyde 179 with 164 gave a quantitative yield of 175 (n = 4). Aldehyde 179 could also be prepared by Vilsmeyer formylation, as well as through a Wittig reaction between 178 and 161. 293The compounds 175 were obtained as cis-trans-isomeric mixtures and were converted to the alltrans-isomers by refluxing with catalytic amounts or iodine in ~ y l e n e . 305 179 180 181 The Wittig reaction between 182 and 161 gave 183 in a statistical mixture of cis-trans-isomers in a 53 YOyield, which was isomerized to the all-trans-isomer with iodine.
The yields are in many cases similar, and which combination is used is determined by the availability of the starting material. The classic Wittig procedure has been followed in the reaction of the ylide from benzyl triphenylphosphonium chloride with various 2-thiophene aldehydes in the preparation of t r ~ n s - 2 - s t y r y l t h i o p h e n e s . 3292- and 3-thiophene aldehyde and 2- and 3-thienylacrolein reacted with 203 to give 204 and 205, respectively, in a 70-80% yield. O 201 /O’CH, Bu36-CH,CH Br \0 ’ CH, I ~ 203 202 I($H=CHCHo S 204 205 The reaction of the ylide from 206 with 3-thiophene aldehyde gave the cisisomer 207 and the trans-isomer 208 in a ratio of 7 : 3.