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Highly Strained Heterocycles Constructed from Boron–Boron Multiple Bonds and Heavy Chalcogens
Author(s) -
Braunschweig Holger,
Constantinidis Philipp,
Dellermann Theresa,
Ewing William C.,
Fischer Ingo,
Hess Merlin,
Knight Fergus R.,
Rempel Anna,
Schneider Christoph,
Ullrich Stefan,
Vargas Alfredo,
Woollins J. Derek
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601691
Subject(s) - chalcogen , electronegativity , boron , tellurium , chemistry , reactivity (psychology) , selenium , nucleophile , electron deficiency , carbon fibers , nitrogen , inorganic chemistry , crystallography , organic chemistry , catalysis , materials science , medicine , alternative medicine , pathology , composite number , composite material
The reactions of a diborene with elemental selenium or tellurium are shown to afford a diboraselenirane or diboratellurirane, respectively. These reactions are reminiscent of the sequestration of subvalent oxygen and nitrogen in the formation of oxiranes and aziridines; however, such reactivity is not known between alkenes and the heavy chalcogens. Although carbon is too electronegative to affect the reduction of elements with lower relative electronegativity, the highly reducing nature of the B−B double bond enables reactions with Se 0 and Te 0 . The capacity of multiple bonds between boron atoms to donate electron density is highlighted in reactions where diborynes behave as nucleophiles, attacking one of the two Te atoms of diaryltellurides, forming salts consisting of diboratellurenium cations and aryltelluride anions.