Synthesis of Azaphosphinines by Directed Inverse‐Electron‐Demand Hetero‐Diels–Alder Reactions with Na(OCP) | Zendy

Hansmann Max M. | Zendy

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Synthesis of Azaphosphinines by Directed Inverse‐Electron‐Demand Hetero‐Diels–Alder Reactions with Na(OCP)

Author(s) -

Hansmann Max M.

Publication year - 2018

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201802173

Subject(s) - chemistry , ionic bonding , diels–alder reaction , inverse , sodium , characterization (materials science) , electron , combinatorial chemistry , medicinal chemistry , organic chemistry , ion , nanotechnology , materials science , mathematics , catalysis , physics , geometry , quantum mechanics

Herein, a straightforward synthetic approach towards azaphosphinines is reported. The synthesis of 1,3‐ and 1,4‐aza‐λ 3 ‐phosphinines as well as 1,2,4‐diaza‐λ 3 ‐phosphinines by inverse‐electron‐demand hetero‐Diels–Alder reactions of sodium 2‐phosphaethynolate [NaOCP] with triazines and tetrazines is studied. In the case of 1,2,4‐triazines a hetero‐D.A. reaction was developed, which relies on a new directing‐group approach based on the complexation of sodium to form an ionic Do→Na‐OCP tether. The first X‐ray characterization data for aza‐λ 3 ‐phosphinines as well as the first phosphinine triflates are presented.

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