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Compr. Heterocyclic Chem. III Vol. 9 Six-membered Rings with by Katritzky A.R., et al. (eds.)

By Katritzky A.R., et al. (eds.)

Content material: v. 1. 3-membered heterocycles, including all fused platforms containing a 3-membered heterocyclic ring / quantity editor, Albert Padwa -- v. 2. 4-membered heterocycles including all fused platforms containing a 4-membered heterocyclic ring / quantity editor, Christian Stevens -- v. three. 5-membered jewelry with one heteroatom including their benzo and different carbocyclic-fused derivatives / quantity editors, Gurnos Jones, Christopher A. Ramsden -- v. four. 5-membered earrings with heteroatoms, each one with their fused carbocyclic derivatives / quantity editor, John Joule -- v. five. 5-membered earrings: triazoles, oxadiazoles, thiadiazoles and their fused carbocyclic derivatives / quantity editor, Viktor V. Zhdankin -- v. 6. different 5-membered earrings with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Viktor V. Zhdankin -- v. 7. 6-membered earrings with one heteroatom, and their fused carbocyclic derivatives / quantity editor, David StC. Black -- v. eight. 6-membered earrings with heteroatoms, and their fused carbocyclic derivatives / quantity editor, R. Alan Aitken -- v. nine. 6-membered earrings with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Kenneth Turnbull -- v. 10. Ring platforms with at the least fused heterocyclic 5- or 6-membered earrings without bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring structures with a minimum of one bridgehead (ring junction) N / quantity editor, Janine Cossy -- v. 12. 5- and 6-membered fused structures with bridgehead (ring junction) heteroatoms concluded: 6-6 bicyclic with one or N or different heteroatoms; polycyclic; spirocyclic / quantity editor, Keith Jones -- v. thirteen. 7-membered heterocyclic earrings and their fused derivatives / quantity editor, George R. Newkome -- v. 14. 8-membered and bigger heterocyclic jewelry and their fused derivatives, different 7-membered jewelry / quantity editor, George R. Newkome -- v. 15. Cumulative topic index

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3 kcal molÀ1) of the azetine 150. Compound 147a is believed to be formed from the addition of the biradical 151 (product of H-migration within 148) to C60 generating 152, which, after a sequence of steps, eventually forms 147a via 147b <2001JOC8187>. Thus, these reactions do not represent direct Diels–Alder additions of C60 to 17m but are reactions of fragmentation products of 17m with the latter. The temperature applied is probably sufficient to allow formation of an energy-rich intermediate (here 149).

1985LA1732>. The following cases were mentioned in CHEC-II(1996) <1996CHEC-II(6)483>.      The addition of 1-diethylaminopropyne and pyrrolidinocyclopentene to 1 and 4-methyl-1,2,3-triazine 86c gives pyridine derivatives <1985LA1732>. [4þ2] Cycloadditions of electron-rich and -poor dienophiles (1-diethylaminopropyne, phenylethyne, phenyl vinylsulfone, ketene diethylketal) to 4,6-dimethyl-1,2,3-triazine 17m at 180  C are mentioned. 11) alone but also with a prefragmentation to 2,4-dimethylazete and addition of the dienophiles to opposite faces of that intermediate <1985CPB3050, 1990CPB2108>.

The molecular formulas of both products were determined by HR FAB MS (146: C65H7N; 147a: C65H6O), and the structures were established by 1H and 13C NMR as well as by comparison of the UV/Vis spectrum of 146 with that of 1,2-dihydrofullerene <1999JOC3483, 1993CB1061>. Compound 147a also showed a characteristic CTO absorption at 1723 cmÀ1 and its NMR spectra were similar to those of its desmethyl derivative <2000JA8333>. Scheme 10 Thermal reaction of 4,6-dimethyl-1,2,3-triazine with C60. The formation of 146 and 147a and 147b was interpreted in terms of two parallel, independent reaction paths.

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