Enols (1990)

As a part of the ongoing sequence on The Chemistry of practical Groups this quantity follows the traditional structure of past variants, delivering info of reactions and complete assurance of the hot literature. Early chapters care for the theoretical, structural, and stereochemical points of Enols, whereas later chapters discover extra really expert subject matters, together with synthesis, photochemistry, Enols of acids and esters, and biochemistry.

Chapter 1 Theoretical calculations (pages 1–74): Yitzhak Apeloig
Chapter 2 Thermodynamics of enols (pages 75–93): J. Peter Guthrie
Chapter three The chemistry of ionized enols within the gasoline part (pages 95–146): Frantisek Turecek
Chapter four NMR, IR, conformation and hydrogen bonding (pages 147–305): B. Floris
Chapter five The new release of volatile enols (pages 307–322): Brian Capon
Chapter 6 Keto–enol equilibrium constants (pages 323–398): Jean Toullec
Chapter 7 Kinetics and mechanism of enolization and ketonization (pages 399–480): James R. Keeffe and A. Jerry Kresge
Chapter eight Isolable and comparatively reliable basic enols (pages 481–589): Harold Hart, Zvi Rappoport and Silvio E. Biali
Chapter nine Photochemical reactions regarding enols (pages 591–638): Alan C. Weedon
Chapter 10 Enols of carboxylic acids and esters (pages 639–650): A. F. Hegarty and P. O'Neill
Chapter eleven The biochemistry of enols (pages 651–689): John P. Richard
Chapter 12 Organometallic chemistry of enols (pages 691–711): David Milstein
Chapter thirteen Structural chemistry (pages 713–764): Gastone Gilli and Valerio Bertolasi

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2% of the keto tautomer6'. To understand the mode of interaction between acetylacetone and triethylamine they carried out ab initio calculations, at the 4-3 1G level, on the interaction between malondialdehyde (a model for acetylacetone) and ammonia (a model for triethylamine)60. The lowest-energy malondialdehyde-NH, complex is computed to be a hydrogenbonded arrangement (30), where NH, acts in the capacity of both acceptor and donor60. As the latter role is not available to triethylamine, which does not have N-H bonds, complexes of type 30 cannot be important for the acetylacetone-triethylamine pair.

Formal analogy with the effect of alkyl groups suggests that an u-silyl substituent would increase AE(eno1~ a r b o n y l )However, ~. 1 kcalmol-' lower than for the 9b-12b pair. The effect of a Me,Si group is similar4'. 0 CH,=C(OH)SiH, I1 CH,CSiH, (274 (27b) The reduction of AE is mainly due to the destabilizing effect of an a-silyl group in the ketone. 8 kcalmol- (equation 15, X = SiH,) ' 1. 3 kcalmol-' (equation 15, X = CH,). 6 kcal mol-I by a methyl group (equation 13, X = CH,), also contributing to the reduction of AE by a-silyl substitution.

0 II CH,CH,CR (13) (a)R = H; (b) R = Me; (c) R = Et; (d) R = i-Pr; (e) R = t-Bu The effect of a P-methyl substituent on the keto-enol equilibrium is obtained by comparing the 102-13 (or 10E-13) energy differences with the analogous 9-12 energy differences [see AAE(b-CH,) values in Table 81. The following conclusions can be extracted from the calculations: (a) In both series AE is smaller for the aldehyde than for the ketones. 4 kcal mol- ' for R = t-Bu. In the E series the p-methyl effect is as expected larger, especially for R = t-Bu.

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