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Adduct of NacNacAl with Benzophenone and Its Coupling Chemistry
Author(s) -
Dmitrienko Anton,
Britten James F.,
Spasyuk Denis,
Nikonov Georgii I.
Publication year - 2020
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.201903719
Subject(s) - benzophenone , adduct , chemistry , trimethylsilyl azide , quinoline , nitrile , azide , tetrazole , cleavage (geology) , aldimine , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , fracture (geology) , composite material , catalysis
Abstract Reaction of NacNacAl (NacNac=[DippNC(Me)CHC(Me)NDipp] − ) with one equivalent of benzophenone affords a ketylate species NacNacAl(η 2 (C,O)‐OCPh 2 ) that undergoes easy cyclization reactions with unsaturated substrates. The scope of substrates included benzophenone, aldimine (PhNC(Ph)H), quinoline, phenyl nitrile, trimethylsilyl azide, and a saturated cyclic thiourea. The latter substrate reacted by an unusual C−N cleavage that left the C=S functionality intact. The new products were characterized by NMR spectroscopy and X‐ray diffraction analysis.