Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles

T. A. Podrugina; A. S. Pavlova; D. S. Vinogradov; M. V. Shuvalov; I. D. Potapov; I. I. Levina; A. V. Mironov; R. Gleiter

doi:10.1007/s11172-019-2384-8

Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles

Authors: Podrugina T.A.¹, Pavlova A.S.¹, Vinogradov D.S.¹, Shuvalov M.V.¹, Potapov I.D.¹, Levina I.I.², Mironov A.V.¹, Gleiter R.³
Affiliations:
1. Department of Chemistry, Lomonosov Moscow State University
2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences
3. Institute of Organic Chemistry of the Heidelberg University
Issue: Vol 68, No 2 (2019)
Pages: 284-292
Section: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/243245
DOI: https://doi.org/10.1007/s11172-019-2384-8
ID: 243245

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Abstract

The reactions of mixed ylides containing a diazonium fragment and an "onium" group of different nature with nucleophiles were studied. In the iodonium-diazonium and sulfoniumdiazonium ylide, the nucleophile first of all substitutes the iodonium and sulfonium group. A series of hetaryl-substituted phosphazines was obtained by a one-pot process of nucleophilic substitution in a diazonium-iodonium ylide with subsequent nucleophilic addition of triarylphosphine at the diazo group.