Benzofuroxans, Indole Grignard Reagents, Isoindoles by Katritzky, Boulton

By Katritzky, Boulton

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Yavari, I. J. Am. Chem. Soc. L. J. Org. Chem. W. J. Org. Chem. 1980, 45, 2511. I. Chem. Rev. T. Tetrahedron Lett. ; van Veldhuizen, B. J. Org. Chem. 1982, 47, 963. B. Acc. Chem. Res. 2003, 36, 255. ; Griller, D. Adv. Free Radical Chem. A. Chem. Rev. W. J. Chem. Educ. J. Determination of Organic Structures by Physical Methods, Vol. 3, Academic Press, NY, 1971, pp. 207–245. 1 kcal –2829 kJ  Fig. 11. Calculation of the heat of atomization of ethane at 25 C. ’’91 Whether measured or calculated, there is no question as to what D values mean.

These deviations occur because of slightly different hybridizations, that is, a carbon bonded to four other atoms hybridizes one s and three p orbitals, but the four hybrid orbitals thus formed are generally not exactly equivalent, nor does each contain exactly 25% s and 75% p character. 80 Of course, in strained molecules, the bond angles may be greatly distorted from the ideal values (see p. 216). For oxygen and nitrogen, angles of 90 are predicted from p2 bonding. However, as we have seen (p.

Chem. Phys. 1967, 47, 3485. S. J. Phys. Chem. Ref. Data 1972, 1, 221–277. C. The Chemical Thermodynamics of Organic Compounds, Wiley, NY, 1969. 6 (or 341). A consideration of heats of atomization of isomers also illustrates the difficulty. 4 kcal molÀ1 (339, 342, 345 kJ molÀ1), respectively, even though all of them have twelve CÀ ÀH bonds and four CÀ ÀC bonds. These differences have been attributed to various factors caused by the introduction of new structural features. Thus isopentane has a tertiary carbon whose CÀ ÀH bond does not have exactly the same amount of s character as the CÀ ÀH bond in pentane, which for that matter contains secondary carbons not possessed by methane.

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