By Richard A. Jones

Actual and Theoretical points of 1H-Pyrroles (D. Chadwick).

The Synthesis of 1H-Pyrroles (G. Bean).

Reactivity of the 1H-Pyrrole Ring approach (A. Jackson, et al.).

actual and Theoretical features, Synthesis, and Chemical Reactivity of 2H- and 3H-Pyrroles (M. Sammes).

Chapter 1 actual and Theoretical features of 1H?Pyrroles (pages 1–103): Derek J. Chadwick
Chapter 2 The Synthesis of 1H?Pyrroles (pages 105–294): Gerritt P. Bean
Chapter three Reactivity of the 1H?Pyrrole Ring method (pages 295–548): Anthony H. Jackson, Anthony H. Jackson, Marino Artico, Hugh J. Anderson, Charles E. Loader, Albert Gossauer, Petr Nesvadba and Nicholas Dennis
Chapter four actual and Theoretical elements, Synthesis, and Chemical Reactivity of 2H? and 3H?Pyrroles (pages 549–728): Michael P. Sammes

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Additional info for Chemistry of Heterocyclic Compounds: Pyrroles, Part One: The Synthesis and the Physical and Chemical Aspects of the Pyrrole Ring, Volume 48

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Refs. 295, 296, 314, and 315 and references cited therein). , Refs. 262,300, and 3 16 and references cited therein). 20. 5" -a - (i "C,D, solvent. bData from Ref. 279. 21. 05 respectively, whereas the spectrum of polypyrrole doped with BF; does not show any structure; the C-a and C-b resonances are almost coincident at 123-126 ppm. 3. 00104 for "N relative to 'H = 1) have discouraged widespread studies of these nuclei. Additionally, spin-lattice relaxation times for the 'N nucleus can be very long (typical literature values range from 40 to 60 s for pyrrole 15N,compared with ca.

The conformational energy of polypyrrole as a function of interannular torsion angle has been mapped by molecular mechanics calculation^^^ and the crystal packing energy minimized as a function of the unit cell variables and the chain setting angle (the angle between the molecular plane and the crystal b axis). The calculations indicate that the planar conjugated structure is the most stable and provide energetically feasible monoclinic and orthorhombic unit cells. 3. MOLECULAR STRUCTURE The planarity and C, symmetry of pyrrole follow from analyses of the microwave spectra of pyrrole itself and of six derivatives labeled with 'H, I3C, and 15N isotopes.

Whereas in 23 where there is little steric hindrance between abutting groups so that both the ester groups are coplanar with the pyrrole ring, steric hindrance in 24 and 25 forces, in both cases, the P-carbonyl-containing substituent out of the ring plane (to the extent of ca. 60"in 24 and ca. , the ketone function in the latter is almost orthogonal to the pyrrole ring). Nonetheless, the a-carbonylcontaining substituent remains coplanar in both compounds. The a-phenyl rings in 24 and 25 deviate from coplanarity with the pyrrole ring by approximately 36" and 25", respectively.

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Chemistry of Heterocyclic Compounds: Pyrroles, Part One: The by Richard A. Jones
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