An unusually stable pyridine-2-selenenyl chloride: structure and reactivity

Bromination of bis(pyridin-2-yl) diselenide in methylene chloride: the reaction mechanism and crystal structures of 1H-pyridine-2-selenenyl dibromide and its cycloadduct with cyclopentene (3aSR,9aRS)-2,3,3a,9a-tetrahydro-1H-cyclopenta[4,5][1,3]selenazolo[3,2-a]pyridinium bromide

“…Determination of the factors providing the stability of organochalcogenyl halides is known to be an urgent challenge in general (Khrustalev et al, 2014(Khrustalev et al, , 2016. The structural features of 2-pyridine-selenenyl and -tellurenyl chlorides have been described by us in detail (Borisov et al, 2010;Khrustalev et al, 2014Khrustalev et al, , 2016. Moreover, we have proposed a probable mechanism of the reaction including the interaction of selenenyl bromide 1* with methanol producing hydrogen bromide and methyl selenite (Fig.…”

“…Previously we have developed an approach to the synthesis of [1,3]thia(selen,tellur)azolo[3,2-a]pyridin-4-ium derivatives via heterocyclization of unsaturated compounds and 2-pyridinesulfenyl, selenenyl and tellurenyl chlorides with ring closure through the nitrogen atom of the pyridyl fragment (Borisov et al, 2010(Borisov et al, , 2012a. In this case, our studies have paid particular attention to clarifying the structural characteristics of the reagents used (Borisov et al, 2010;Khrustalev et al, 2014Khrustalev et al, , 2016. Determination of the factors providing the stability of organochalcogenyl halides is known to be an urgent challenge in general (Khrustalev et al, 2014(Khrustalev et al, , 2016.…”

“…In this case, our studies have paid particular attention to clarifying the structural characteristics of the reagents used (Borisov et al, 2010;Khrustalev et al, 2014Khrustalev et al, , 2016. Determination of the factors providing the stability of organochalcogenyl halides is known to be an urgent challenge in general (Khrustalev et al, 2014(Khrustalev et al, , 2016. The structural features of 2-pyridine-selenenyl and -tellurenyl chlorides have been described by us in detail (Borisov et al, 2010;Khrustalev et al, 2014Khrustalev et al, , 2016.…”

The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide: the first monomeric organoselenenyl chloride stabilized by an intramolecular secondary Se...O interaction

“…interactions with the formation of dimers (Borisov et al, 2010a,b,c;Khrustalev et al, 2016). Herein, we report on the synthesis and structural characterization of the first monomeric 2-(chloroselanyl)pyridine 1-oxide stabilized by an intramolecular secondary SeÁ Á ÁO interaction.…”

“…An essential aspect of the chemistry of selenenyl halides is the factors responsible for the stability of these reagents (Coles, 2006;Mukherjee et al, 2010;Nakanishi et al, 2013;Takaluoma et al, 2015). Recently, we have developed a new effective method for the stabilization of heteroarenselenenyl and -tellurenyl chlorides by the transformation of them to T-shaped zwitterionic adducts with hydrochloric acid (Khrustalev et al, 2012(Khrustalev et al, , 2014(Khrustalev et al, , 2016. Moreover, we have established another stabilization method of heteroarenselenenyl and -tellurenyl chlorides by intermolecular secondary ChÁ Á ÁN (Ch = Se, Te)…”