Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a stepwise transition state more than the energy of the competing concerted pathway. This energy shift induces CSI to react with monofluoroalkenes by a one-step process. The low reactivity of CSI with monofluoroalkenes, stereospecific reactions, the absence of 2:1 uracil products with neat fluoroalkenes, and quantum chemical calculations support a concerted pathway.

No abstract

No abstract

The cyclization of a range of aniline and phenol derivatives to indoles and benzofurans is presented. Advantages of this reaction are the use of only 2 mol% catalyst in most cases and the unprecedented ability of a cycloisomerization catalyst to perform hydration or deuteration in the same reaction. -(NAIR, R. N.; LEE, P. J.; REINGOLD, A. L.; GROTJAHN*, D. B.; Chem. Eur.