15645-75-7Relevant articles and documents
A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N-O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products
Ieronimo, Gabriella,Mondelli, Alessandro,Tibiletti, Francesco,Maspero, Angelo,Palmisano, Giovanni,Galli, Simona,Tollari, Stefano,Masciocchi, Norberto,Nicholas, Kenneth M.,Tagliapietra, Silvia,Cravotto, Giancarlo,Penoni, Andrea
, p. 10906 - 10920 (2014/01/06)
The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between o-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.
Theory-guided discovery of unique chemical transformations of cyclopropenes
Weatherhead-Kloster, Robin A.,Corey
, p. 171 - 174 (2007/10/03)
(Chemical Equation Presented) Chiral 2-cyclopropenyl-4-tolyl sulfones, available by the [2 + 1]-cycloaddition of tosyldiazomethane to acetylenes under catalysis by the Rh(II) complex 1, provide a number of unusual transformations and useful chiral product
PREPARATION AND REACTIVITY OF ARYLSULFONYL SUBSTITUTED CYCLOPROPENES
Padwa, Albert,Wannamaker, M. Woods
, p. 6139 - 6156 (2007/10/02)
A study of the cycloaddition behaviuor of several arylsulfonyl substituted alkynes with 2-diazopropane has been carried out.These activated acetylenes react to give 3H-pyrazoles which extrude nitrogen on photolysis to produce cyclopropenes in high yield.Soft nucleophiles such as thiophenoxide readily add to the activated pi-bond to give thiophenyl substituted cyclopropanes.Reaction of 1-phenylsulfonyl-2,3,3-trimethylcyclopropene with n-butyllithium followed by alkylation with various electrophiles produces arylsulfonyl substituted methylene cyclopropanes.These compounds undergo thermal rearrangement to the thermodynamically more stable isopropylidene cyclopropane.
REACTIVITY OF PHENYLIODONIUM BIS(ARYLSULPHONYL)METHYLIDES TOWARDS ALKENES AND ALKYNES: CRYSTAL STRUCTURE OF 9-PHENYLSULPHONYL-1,2,3,4,4a,9a-HEXAHYDRO-1,4-METHANOFLUORENE
Hatjiarapoglou, Lazaros,Varvoglis, Anastassios,Alcock, Nathaniel W.,Pike, Graham A.
, p. 2839 - 2846 (2007/10/02)
Thermal or photochemical reactions of phenyliodonium bis(arylsulphonyl)methylides with alkenes lead normally to gem-(arylsulphonyl)cyclopropanes.Norbornene and trans-stilbene, however, afford 1-(phenylsulphonyl)indane derivatives.The crystal structure of the title compound /= 3.0>> confirmed the identity of the product with norbornene.Diarylacetylenes give 1-(arylsulphonyl)indenes.Thermal decomposition of the ylides involves a new rearrangement, with formation of aryl arenethiosulphonates.