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On the ozonolysis of unsaturated tosylhydrazones as a direct approach to diazocarbonyl compounds

Abstract:

The scope and limitations are described of reacting unsaturated tosylhydrazones with O3 followed by Et3N for the generation of 1,4- and 1,5-diazocarbonyl systems. Tosylhydrazones, from tosylhydrazide condensation with readily available δ- and ε-unsaturated α-ketoesters, led in the former case to a 2-pyrazoline whereas the latter cases led to α-diazo-ε-ketoesters, although a terminal alkene produced a tetrahydropyridazinol. Using the ozonolysis–Et3N strategy, tosylhydrazones from cyclic enones...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c8ob00435h

Authors


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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Role:
Author
More from this funder
Name:
Engineering and Physical Sciences Research Council
Grant:
EP/L505031/1
More from this funder
Name:
Higher Education Commission of Pakistan
Publisher:
Royal Society of Chemistry
Journal:
Organic and Biomolecular Chemistry More from this journal
Volume:
16
Issue:
16
Pages:
2876-2884
Publication date:
2018-04-03
Acceptance date:
2018-03-20
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Pubs id:
pubs:831865
UUID:
uuid:62dd4d0d-c90f-4dba-bbe2-b433503a9846
Local pid:
pubs:831865
Source identifiers:
831865
Deposit date:
2018-03-27

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