Novel five- and six-membered ring phosphorus-selenium heterocycles from selenation of amido-Schiff bases

Guoxiong Hua, David B. Cordes, Alexandra M. Z. Slawin, J Derek Woollins

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)
3 Downloads (Pure)

Abstract

Woollins’ reagent, [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide], serving as a selenating-reductive cycloaddition reagent, reacts with nonconjugated amido-Schiff bases to give the corresponding six-membered 1,3,4-selenadiazoles via a ring-expansion accompanied by an additional selenation/cyclization to the imine bond and C═O group; meanwhile, under the same reaction conditions, the selenation of conjugated amido-Schiff bases leads to a series of fused heterocycles with two five-membered rings. Eight single-crystal X-ray structures confirming the formation of these five- and six-membered heterocycles are discussed.
Original languageEnglish
Pages (from-to)11737-11744
Number of pages8
JournalACS Omega
Volume5
Issue number20
Early online date12 May 2020
DOIs
Publication statusPublished - 26 May 2020

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