I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Named Reactions in Organic Synthesis
Pericyclic and photochemical reactions
Other featured pericyclic reactions:
Featured photochemical reactions:
In 1974 the American chemist Larry Overman reported the thermal and mercuric ion catalysed rearrangement of allylic trichloroacetimidates to create the corresponding trichloroacetamides. Subsequently the 1,3-transposition of alcohol and amine functionalities via [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates became known as the Overman rearrangement. The allylic trichloroacetimidates are readily prepared by treating the corresponding alcohols with trichloroacetonitrile in the presence of catalytic amounts of a base such as DBU.
In recent decades the Overman rearrangement has become an important carbon nitrogen bond forming reaction used in many synthesis campaigns. For example during the total synthesis of sphingofungin E by N. Chida and colleagues the stereocenter at C5 was formed using the Overman rearrangement of an allylic trichloroacetimidate derived from diacetone-D-glucose.
Mechanism of the Overman rearrangement:
Other reaction categories:
Some relevant Alfa Aesar products for the Overman rearrangement:Trichloroacetonitrile, 98%
n-Butyllithium, 2.2M in hexane
Xylenes, mixed, 97+%
Xylenes, ACS, 98.5+% (Assay, isomers plus ethylbenzene
We have many allylic alcohols in our portfolio.