Rearrangements of cyclopentadienyl cyanates, isocyanates and their thio-,seleno-, and telluro-analogs View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2009-08

AUTHORS

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

ABSTRACT

Dynamic NMR spectroscopy revealed that pentaphenylcyclopentadienyl isoselenocyanate undergoes reversible hetero-Cope rearrangement (ΔG≠408 K ∼ 22 kcal mol−1, C6D5CD3) giving isomeric selenocyanate in which 1,5-sigmatropic shifts of the SeCN group along the perimeter of the cyclopentadiene ring occur (ΔG≠298 K = 16.7 kcal mol−1, C6D5CD3). On the contrary, pentaphenylcyclopentadienyl iso(thio)cyanates Ph5C5NCO and Ph5C5NCS are structurally rigid compounds on the NMR time scale. The energy barrier to the 3,3-shift of the isoselenocyanate group in pentaphenylcyclopentadienyl derivative Ph5C5NCSe (ΔG298 K≠ = 17.9 kcal mol−1) caclulated using the B3LYP/6-31G** method is 7.6 kcal mol−1 lower than for the unsubstituted analog H5C5NCSe. More... »

PAGES

1713-1723

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-009-0237-6

DOI

http://dx.doi.org/10.1007/s11172-009-0237-6

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1046956591


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