By Salo Gronowitz
Vinylthiophenes and Thienylacetylenes (S. Gronowitz & A.-B.
Organometallic Derivatives of Thiophenes (T. Frejd).
Syntheses, Reactions, and actual houses 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
Read or Download Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Five, Volume 44 PDF
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Extra info for Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives, Part Five, Volume 44
The methyl group in the o-methylnitrothiophenes shows varying reactivity toward aldehydes under base catalysis. 3-Methyl-2-nitrothiophene, in contrast to o-methylnitrotoluene, reacts to give vinyl derivatives. 279 R=H R=C,H, R =p-CH,OCbHa R=p-CICbH~ R = 2-Th 151 I50 On the other hand, applying these reaction conditions to 2-thiophene aldehyde gave only low yields of the desired product, and much tar. 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.
Introduction An often used conventional route to thienylvinyl derivatives 284 is the dehydration of 1-(thieny1)alkanols 283. Secondary alcohols have often been prepared from thienyl ketones (obtained by FriedelLCrafts acylation of thiophenes) through reduction with LiAlH, or NaBH,. 283 284 Alternatively, the alcohols 283 can be obtained through the reaction of Grignard reagents with thiophene aldehydes, thiophene ketones, through the reaction of thienyllithium, or thiophene magnesium derivatives with aldehydes, ketones, or esters.
74 183220,2313265-270 CN R = H, CH,, OCH,, CH2C,H5, C,H5 143 11. Preparation of Vinylthiophenes 33 The condensation of 5-chloro-2-thenyl cyanide with carbon disulfide in the presence of sodium hydride led to the hydrated salt 144. 275 145 146 8. ”~ 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.
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