17420-00-7Relevant academic research and scientific papers
Substituted N-aryl alk-1-enesulfinamides: Preparation, properties and conversion into the corresponding indole compounds [1]
Baudin, Jean-Bernard,Commenil, Marie-Gabrielle,Julia, Sylvestre A.,Lorne, Robert,Mauclaire, Laurent
, p. 329 - 350 (2007/10/03)
Reaction of vinylic organometallic derivatives with N-sulfinyl arenamines 2 affords the title sulfinamides 3. On heating their solutions in selected solvents to 80-124 °C, these sulfinamides are converted into the corresponding indoles 6, probably via a [3.3]-sigmatropic rearrangement to intermediates VIII which undergo an intramolecular carbophilic reaction of the nitrogen atom with the neighboring sulfine group, followed by elimination of HSOH. The triethyloxonium tetrafluoroborate- or boron trifluoride etherate catalyzed conversion 3 → 6 can be carried out at a much lower temperature. Elsevier,.
1,2-Thiazines and Related Heterocycles. Part 1. An Investigation of the Cycloadditions of N-Sulphinylanilines with 1,4-Epoxy-1,4-dihydronaphthalene and Other Alkenes
Hanson, Peter,Lewis, Robin J.,Stone, Thomas W.
, p. 1719 - 1724 (2007/10/02)
Evidence is adduced from the character of the alkenes which cycloadd to N-sulphinylanilines and from a kinetic investigation of the reactions of N-sulphinylanilines with 1,4-epoxy-1,4-dihydronaphthalene, examining the effects upon reaction rate of solvent polarity, temperature, and substitution in the N-sulphinylanilines, that the cycloadditions are pericyclic reactions of Diels-Alder type with inverse electron demand.A degree of charge separation in the transition state is indicated but this is small and confined essentially to the sulphinylaniline moiety.
