Conversion of Phenols into Selenophenols: Seleno Newman–Kwart Rearrangement

Abstract

A 'Se'lling point: The first thermally induced OAr →SeAr migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state. The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

Selenium‐NMR Spectroscopy in Organic Synthesis: From Structural Characterization Toward New Investigations

“…For instance, a benzylic thio‐ and seleno‐Newman‐Kwart rearrangement was studied to provide mechanistic insights [149] . In this recent work, Pittelkow and co‐workers have observed a fundamental change in the rearrangement mechanism when altering the phenyl group of the benzylic species [150] . The reaction was carried using both elements (S or Se), and the reaction kinetic was discussed based on the substrate scope.…”

“…[149] In this recent work, Pittelkow and co-workers have observed a fundamental change in the rearrangement mechanism when altering the phenyl group of the benzylic species. [150] The reaction was carried using both elements (S or Se), and the reaction kinetic was discussed based on the substrate scope. The progress of the rearrange- ment reaction was easily monitored by 1 H NMR spectroscopy, although the 77 Se NMR analysis was used to corroborate the results and afford new insights (Figure 20).…”

A “weak acid and weak base” type fluorescent probe for sensing pH: mechanism and application in living cells

“…[12][13][14][15] An optical probe, especially a uorescent probe, is one of the most powerful tools for detecting pH in cells for its advantages of simple operation, high sensitivity, and temporal resolution. [16][17][18] Many pH uorescent probes have been designed. There are two classes of synthetic pH probesone for acidic organelles (such as, lysosomes) functioning in the pH range of 4.00-6.00, and another for cytosol that works in the pH range 6.80-7.40.…”

A Straightforward Access to Stable β‐Functionalized Alkyl Selenols

“…Among the variety of organoselenium compounds, aryl selenols are of particular interest for their use in catalysis, in coordination and inorganic chemistry . As a prominent example aryl selenols take part in asymmetric transformations catalyzed by chiral complexes .…”