Download Chemistry of Heterocyclic Compounds: Thiophene and Its by Salo Gronowitz PDF

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 comparable 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 houses of Bithienyls and Polythienyls and heavily comparable Compounds (pages 755–905): Rolf Hakansson

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Additional resources for Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Five, Volume 44

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280 In the condensation with formaldehyde, 2-methyl-3-nitrothiophene reacted differently and gave trans- 1,2bis-(3-nitro-2-thienyl)cyclobutaneas the main product,280together with 3-nitro2-vinylthiophene. 280 9. Wittig Reaction A. 282 2 9 1 The starting triphenylphosphonium halides were easily obtained by the reaction of thenyl halides with triphenyl phosphine. The thenyl halides were 11. Preparation of Vinylthiophenes 35 prepared by chloromethylation of thiophenes or side-chain bromination of methylthiophenes.

The yields in the R = 3-Th R: 2-Th R = 2-FU R = -CH=CHPh R=C,H, R = 3-Th R = 2-Th R = 5-CI-2-Th R =-CHXHPh 148 147 R=H R=OCH, R=CI 149 34 Vinylthiophenes and Thienylacetylenes condensation with cinnamaldehyde were very low. Dinitrodistyrylthiophenes 149 were prepared in an 8 6 8 5 % yield from 2,5-dimethyl-3,4-dinitrothiophene and the appropriate aldehyde, normally using no solvent and pyrrolidine as a catalyst. The methyl group in the o-methylnitrothiophenes shows varying reactivity toward aldehydes under base catalysis.

244 100 99 The condensation of 2- and 3-thiophene aldehyde with 101, a malonaldehyde equivalent, gave 102 in a 86% and a 75% yield, respectively, using acetic anhydride and zinc chloride for the c ~ n d e n s a t i o n . 247 + (CH3)zNCH=CH-CH=N(CH3)zC10~ 101 102 y)0 II ' W C H 0 + HzC,C II 0 103 104 105 26 Vinylthiophenes and Thienylacetylenes X=H, 107 106 6. 248-2s3These products have been used for the preparation of benzo[b]thiophene derivatives. This cyclization was also utilized as a proof of the stereochemistry of the acid 108.

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