Fast and reversible migrations of N,S-centered groups around the perimeter of cyclopropene and cycloheptatriene rings View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1998-05

AUTHORS

V. I. Minkin, I. E. Mikhailov, G. A. Dushenko, O. E. Kompan, A. Zschunke

ABSTRACT

The kinetics and mechanism of circumambulatory rearrangements of N-centered (NCS) and S-centered (SPh, SC3Ph3, SC(OEt)=S) groups in corresponding derivatives of 1,2,3-triphenylcyclopropene and cycloheptatriene were studied by dynamic1H and13C NMR spectroscopy. Migrations of the isothiocyanate group occur by the dissociation-recombination mechanism with intermediate formation of a tight ionic pair. Migrations of the phenylthio group around the perimeter of cyclopropene and cycloheptatriene rings occur by the 1,2-shift mechanism. It was found that rearrangements of theO-ethyl dithiocarbonate group inS-(1,2,3-triphenylcyclopropen-3-yl)-O-ethyl dithiocarbonate occur by the 3,3-sigmatropic shift mechanism. The molecular and crystal structure ofO-ethylS-(1,2,3-triphenylcyclopropen-3-yl) dithiocarbonate was studied by X-ray analysis. More... »

PAGES

884-894

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02498157

DOI

http://dx.doi.org/10.1007/bf02498157

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1037115280


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