53188-69-5Relevant articles and documents
Sulfone–Metal Exchange and Alkylation of Sulfonylnitriles
Yang, Xun,Nath, Dinesh,Gau, Michael R.,Steward, Omar W.,Fleming, Fraser F.
supporting information, p. 7257 - 7260 (2017/06/13)
The first general sulfone–metal exchange is described. Treating substituted 2-pyridylsulfonylacetonitriles with either BuLi or Bu3MgLi generates metalated nitriles that efficiently intercept a variety of electrophiles to afford quaternary nitriles. The 2-pyridylsulfone is critical for the sulfone–metal exchange because chelation anchors the organometallic proximal to the electrophilic, tetrasubstituted sulfone to override complex-induced deprotonation. Alkylating commercial 2-pyridinesulfonylacetonitrile with mild bases, either K2CO3 or DBU, and subsequent sulfone–metal exchange and alkylation rapidly assembles quaternary nitriles by three alkylations, only one of which requires an organometallic reagent.
Rearrangements of substituted 3-aza-1,2,5-hexatrienes. 3. The scope and versatility of an extremely mild 3-aza-Cope reaction
Walters, Michael A.,Hoem, Andrew B.,McDonough, Colleen S.
, p. 55 - 62 (2007/10/03)
An investigation of the [3,3]-sigmatropic reaction of substituted 3-aza-1,2,5-hexatrienes to give 4-pentenenitriles is presented. This reaction has been found to occur under a wide variety of reactions conditions (10 are reported) starting from readily av
