Theoretical and experimental studies on the structure and isomerization of isocyano and cyano cyclopolyenes View Full Text


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Article Info

DATE

2008-10

AUTHORS

O. I. Mikhailova, G. A. Dushenko, I. E. Mikhailov, R. M. Minyaev, V. I. Minkin

ABSTRACT

Quantum-chemical calculations in terms of the density functional theory showed that cyclopolyenyl isocyanides RNC are considerably less stable than the corresponding cyanides and that they are capable of undergoing RNC → RCN isomerization according to both 1,2-shift mechanism (cyclopropenyl and cyclopentadienyl isocyanides; ΔE≠ = 35.0 and 37.5 kcal/mol, respectively) and previously unknown 2,5-sigmatropic shift mechanism (cycloheptatrienyl isocyanide, ΔE≠ = 26.4 kcal/mol). Migration of cyano group in the cyclopentadiene and cycloheptatriene systems follows the 1,5-sigmatropic shift pattern. The activation barrier to 1,5-shift of cyano group around the cycloheptatriene ring was estimated by dynamic NMR in deuterated nitrobenzene (ΔG190°C≠ = 26.5 kcal/mol). More... »

PAGES

1451-1463

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428008100096

DOI

http://dx.doi.org/10.1134/s1070428008100096

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1006571619


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