Tosylhydrazone

A tosylhydrazone in

tosylhydrazine.^[1]

Synthesis

As an example camphor tosylhydrazone is synthesised from

tosylhydrazine in ethanol with hydrochloric acid catalysis.^[2]

Reactions

Hydrolysis is the reverse reaction of formation with regeneration of the carbonyl compound.

In the

reduced to the corresponding alkanes with reagents such as sodium borohydride and borane

.

Tosylhydrazone salts can react with metals to form

metal carbene

through the diazo intermediate.

Tosylhydrazones are also starting materials for certain

diazo

intermediateformed by decomposition of the tosylhydrazone forms a palladium-carbene complex with the oxidative addition complex of palladium with the aryl halide. Using this powerful method it is possible to access bioactive compounds.^[9] ^[10]

References

OCLC 642506595

^ 2-Bornene, Organic Syntheses, Coll. Vol. 6, p.172 (1988); Vol. 51, p.66 (1971). link

doi:10.1021/ja034606+

doi:10.1002/ejoc.200400700

doi:10.1021/ol0164177

ClFeTPP
the amount of trans isomer increases to 33%
doi:10.1002/anie.201007961

doi:10.1002/anie.200701815

doi:10.1021/ol101639g

doi:10.1039/C2OB26253C

Retrieved from "https://en.wikipedia.org/w/index.php?title=Tosylhydrazone&oldid=1118577259"

[1] OCLC 642506595

[2] 2-Bornene, Organic Syntheses, Coll. Vol. 6, p.172 (1988); Vol. 51, p.66 (1971). link

[3] doi:10.1021/ja034606+

[4] doi:10.1002/ejoc.200400700

[5] doi:10.1021/ol0164177

[6] ClFeTPP
the amount of trans isomer increases to 33%

[7] doi:10.1002/anie.201007961

[8] doi:10.1002/anie.200701815

[9] doi:10.1021/ol101639g

[10] doi:10.1039/C2OB26253C

[1]

[2]

[9]

[10]