New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide

Abstract

Cycloadditions and other reactions of compounds containing the groups NSO and NSN are reviewed.

An Adduct of Sulfur Monoxide to a Frustrated Sn/P Lewis Pair

“…Only recently, methods were developed to transfer SO from nitrogen-bound forms, in particular sulfinylimine-type compounds. [5] Cummins et al found a way of SO transfer from an anthracene-based N-sulfinylhydrazine onto 3,5-ditert-butyl-1,2-benzoquinone and 2,3-dimethyl-1,3-butadiene at elevated temperature. [6] This was preceded by work of Stephan et al, who observed adduct formation between the readily available N-sulfinyl-p-toluidine, p-TolNSO, and the frustrated Lewis pairs (FLPs) P(tBu) 3 /B(C 6 F 5 ) 3 and [(Mes) 2 P-(CH 2 ) 2 B(C 6 F 5 ) 2 ]; the adducts contain P-N(p-Tol)-S-O-B units.…”

Oxidation of diethyl N‐sulfinylphos‐phoramidates

“…The similar transsulfinylation reaction of phenylenediamine and other amines, by the Nsulfinylaniline, was previously reported [28].…”

Novel cycloadducts from the 1,3-dipolar cycloaddition reactions of triazolium-1-imide 1,3-dipoles

“…However, if the carbon atom of the C=N bond also carries an electronwithdrawing group as in CO 2 R, CF 3 or CCl 3 , adducts are formed under the above conditions. 8 Four imines 7a-d were chosen to use as dipolarophiles in the cycloaddition reaction. Of these, three had an electron-withdrawing group 7a-c attached to the carbon, i.e.…”