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Issue 9, 2015
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N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley–Griffith (TPAP) tandem oxidation-Wittig reactions

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Abstract

N,N,N′,N′-Tetramethylethylenediamine dioxide (TMEDAO2) was explored as a more atom economical co-oxidant for the Ley–Griffith oxidation of alcohols to aldehydes. TMEDAO2 was found to selectivity oxidise benzylic and allylic alcohols in comparable yields to that of the standard Ley–Griffith co-oxidant (NMO). Importantly TMEDAO2 facilitated tandem Ley–Griffith-Wittig reactions with stabilised ylides, in good to excellent yields, without the requirement of anhydrous conditions.

Graphical abstract: N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley–Griffith (TPAP) tandem oxidation-Wittig reactions

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Article information


Submitted
16 Jun 2015
Accepted
27 Jul 2015
First published
06 Aug 2015

Green Chem., 2015,17, 4537-4540
Article type
Communication

N,N,N′,N′-Tetramethylenediamine dioxide (TMEDAO2) facilitates atom economical/open atmosphere Ley–Griffith (TPAP) tandem oxidation-Wittig reactions

C. D. G. Read, P. W. Moore and C. M. Williams, Green Chem., 2015, 17, 4537
DOI: 10.1039/C5GC01346A

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