Synthesis of Bis(Phospha-λ5-Azenes) by a Redox-Condensation Reaction. Formation of an Anomalous N-Cyanophospha-λ5-Azene from Urea

Shmuel Bittner, Yonit Assaf, Penina Krief, Martin Pomerantz, Shikang Xi, Malgorzata K. Witczak

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The reaction of diphosphines [Ph2P(CH2)nPPh2; n = 1, 2] with sulfonamides, a phosphinamide, and cyanamide as well as of a dicarboxamide, a disulfonamide, urea, thiourea, and sulfamide with triphenylphosphine in the presence of diethyl azodicarboxylate has been shown to produce bis(phospha-λ5-azenes). In the case of cyanamide with bis(diphenylphosphino)methane a mono-(10) as well as a bis(phospha-λ5-azene) (9) could be prepared. Further, the monophospha-λ5-azene monooxide 11 was also isolated. In the case of thiourea, the monophospha-λ6-azene intermediate was also isolated. The reaction of urea with bis(diphenylphosphino)methane gave the mono-N-cyanophospha-λ5-azene monooxide (11) along with bis(diphenylphosphino)methane dioxide. This is the first observation of a nitrile produced in the reaction of an amide, a phosphine, and diethyl azodicarboxylate at room temperature.

Original languageEnglish
Pages (from-to)1-5
Number of pages5
JournalJournal of Organic Chemistry
Issue number1
StatePublished - 1 Jan 1988


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