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Borabicyclo[3.2.0]heptadiene: A Fused Bicyclic Isomer of Borepin
Author(s) -
Kelch Hauke,
Kachel Stephanie,
Wahler Johannes,
Celik Mehmet Ali,
Stoy Andreas,
Krummenacher Ivo,
Kramer Thomas,
Radacki Krzysztof,
Braunschweig Holger
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201803509
Subject(s) - heteronuclear molecule , alkyne , reactivity (psychology) , bicyclic molecule , chemistry , acetylene , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , catalysis , alternative medicine , pathology , medicine
A new isomer of borepin, identified as 2‐borabicyclo[3.2.0]hepta‐3,6‐diene by single‐crystal X‐ray diffraction and heteronuclear NMR spectroscopy, was obtained by reaction of 1‐mesityl‐2,3,4,5‐tetraphenylborole with the diaminoalkyne bis(piperidyl)acetylene. Analogous reactions of the alkyne with other borole derivatives generated seven‐membered borepins, in which a second equivalent of the alkyne was found to insert into the exocyclic B−C bond. Results of mechanistic DFT studies as well as differences in the reactivity of the boroles toward the diaminoalkyne are discussed.