Selectivity Modulation of the Ley–Griffith TPAP Oxidation with  N ‐Oxide Salts | Zendy

Moore Peter W. | Zendy; Jiao Yanxiao | Zendy; Mirzayans Paul M. | Zendy; Sheng Lexter Ng Qi | Zendy; Hooker Jordan P. | Zendy; Williams Craig M. | Zendy

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Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N ‐Oxide Salts

Author(s) -

Moore Peter W.,

Jiao Yanxiao,

Mirzayans Paul M.,

Sheng Lexter Ng Qi,

Hooker Jordan P.,

Williams Craig M.

Publication year - 2016

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201600453

Subject(s) - tetraphenylborate , chemistry , salt (chemistry) , anhydrous , oxide , crystallization , selectivity , sodium tetraphenylborate , medicinal chemistry , allylic rearrangement , inorganic chemistry , organic chemistry , nuclear chemistry , catalysis , ion

A wide variety of novel non‐hygroscopic N ‐oxide tetraphenylborate salts were synthesized and evaluated as co‐oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non‐anhydrous conditions. The novel DABCOO · TPB (2:1) salt was herein unearthed as a viable competitor to the first‐generation NMO · TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X‐ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N ‐oxide–tetraphenylborate salts could be formed.

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