Chemistry of Heterocyclic Compounds: Thiophene and its by Salo Gronowitz

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By Salo Gronowitz

Syntheses, actual houses and Reactions of Compounds Containing Thiophene-oxygen Bonds (S. Gronowitz, A. Hornfeldt).

Syntheses, actual houses and Reactions of Compounds Containing Thiophene-sulfur Bonds (S. Gronowitz, A. Hornfeldt).

Formyl and Acyl Derivatives of Thiophenes and Their Reactions (R. Scrowston).

Thiophenecarboxylic Acids and Their Derivatives (J. Barker, P. Huddleston).

Side-chain Reactivity of Thiophenes;
Thenyl Derivatives (G. Musumarra).

writer Index.

topic Index.Content:
Chapter I Syntheses, actual houses, and Reactions of Compounds Containing Thiophene—Oxygen Bonds (pages 1–133): Salo Gronowitz and Anna?Britta Hornfeldt
Chapter II Syntheses, actual homes, and Reactions of Compounds Containing Thiophene—Sulfur Bonds (pages 135–307): Salo Gronowitz and Anna?Britta Hornfeldt
Chapter III Formyl and Acyl Derivatives of Thiophenes and their Reactions (pages 309–563): Richard M. Scrowston
Chapter IV Thiophenecarboxylic Acids and their Derivatives (pages 565–973): John M. Barker and Patrick R. Huddleston
Chapter V Side?Chain Reactivity of Thiophenes. Thenyl Derivatives (pages 975–1153): Giuseppe Musumarra

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Extra resources for Chemistry of Heterocyclic Compounds: Thiophene and its Derivatives, Part Three, Volume 44

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5 115-116 81-82 33 65-68 Boiling Point e C / m m H g ) Melting Point ("C) 65 53 75 43 63 72 24 38 90 33 29 48 64 77 93 100 27 90 21 100 38 83 28 92 110 110 292 292 292 134 164 97 94 110 92 106 92 110 96 96 3 111 110 110 110 3 97 89 104 Yield (%) Reference P h) H H 2-Thienyl 2-Fury1 CH3 H H H H H H R4 H CH,CH=CH, H H CH(CH3), H H CN R' (Continued) H CH(CH,)CH=CH, CH,CH=CH--CH, CH,CO,C,H, H C(CH3)3 H H H 9 1-Cyclopentenyl C(C, H,)=CHCH, 10 3-Thienyl-5-CH3 H 8 7 C, TABLE 1. u! N r3 m - m 3 . c? 9 0 0 0 \D 4 I m m * ,,, h ZN U II 3: 3 n CI 3: U II J: 3 n 2 U 0 3: 3: U 3: v $ 3 : UOZZO U zz3: 3:ooo 3: h * P 9 10 11 19 8 5 6 7 4 cn 4-THIOLEN-2-ONES H H H H H H C(CH,), R& = CH, H H CH,C,H, R& = CH,C,H, NO2 H H R; TABLE 2.

However, 154 155 X = H, Br 157 156 Scheme 44 Preparation of Hydroxythiophenes 25 owing to the tendency of 3-thienyllithium derivatives to rearrange to more stable 2-thienyllithium derivatives or to undergo ring-opening reactions, halogen-metal exchange and reaction with the borates must be carried out at - 70°C. In this way 2-alkyl-3-hydro~ythiophenes,~~ various 2,5-dialky1-3-hydro~ythiophenes,~~~~'~~~ and 2-methyl-5-phenyl-3-hydro~ythiophene'~ were prepared. "' From 4-formyl-3-thiopheneboronic acid, the highly unstable 4-hydroxy-3thiophene aldehyde, only characterized by its NMR spectrum, was obtained.

36 In addition, the catalytic effect of various pyridine bases on the tautomeric rearrangement of 262 ( R = CH3) to 263 ( R = CH3) in methanol at various temperatures has been measured, and the activation parameters for the reaction, which follows a general base catalysis pattern, have been calculated. 58 was obtained for the 4-substituted pyridines. The a-substituted pyridines, on the other hand, showed deviations in the Brbnsted diagrams, which were functions of the steric ~ 0 n d i t i o n s .

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