General Characteristics Under acidic conditions, 1,2-diphenylhydrazines are known to rearrange into 4,4’-diaminobiphenyls (benzidines). General References Hofmann, A. W. Proc. Roy. Soc. London ...
Tag Archives: sigmatropic rearrangement
Overman Rearrangement
General Characteristics The trichloroacetimidates of allylic alcohols, prepared using trichloroacetonitrile, undergo thermal or catalyzed [3,3]-sigmatropic rearrangement, which is referred to as the ...
Aza-Cope Rearrangement
General Characteristics Nitrogen-containing 1,5-dienes undergo [3,3]-sigmatropic rearrangement just like the Cope rearrangement of 1,5-dienes. Among these so-called aza-Cope rearrangements, the 3-aza ...
Fischer Indole Synthesis
General Characteristics Upon heating under acidic conditions, aryl hydrazones synthesized from aldehydes/ketones and aryl hydrazines undergo sigmatropic rearrangement and aromatization to give ...
Claisen Rearrangement
General Characteristics The Claisen rearrangement is the [3,3]-sigmatropic rearrangement of allyl vinyl ethers producing γ,δ-unsaturated carbonyl compounds. This reactions is analogous to the Cope ...
Ichikawa Allylcyanate Rearrangement
Characteristics Ichikawa Allylcyanate rearrangement is [3.3] sigmatropic rearrangement of allyl cyanates to isocyanate. The rearrangement begins with dehydration of allyl carbamate by Appel ...
Divergent Total Synthesis of Indoxamycins A, C, and F
He, C.; Zhu, C.; Dai, Z.; Tseng, C.-C.; Ding, H. Angew. Chem. Int. Ed. 2013, 52, 13256–13260. DOI: 10.1002/anie.201307426 The concise and divergent total synthesis of (−)-indoxamycins A, C, and F has ...