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Beiträge zur Chemie des Bors, 218 [1] . Über die Reaktion von 9‐Fluorenyliden‐tetramethylpiperidino‐boran mit Nitrilen und Isonitrilen: Azaborafluoranthene und Ketenimino‐azaborolidine
Author(s) -
Mayer Erwin P.,
Nöth Heinrich
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260708
Subject(s) - chemistry , borane , cycloaddition , medicinal chemistry , ring (chemistry) , boro , stereochemistry , boron , organic chemistry , catalysis
Contributions to the Chemistry of Boron, 218 [1] .–On the Reaction of 9‐Fluorenylidene‐tetramethylpiperidino‐borane with Nitriles and Isonitriles: Azaborafluoranthenes and Ketenimino‐azaborolidines 9‐Fluorenylidene‐tetramethylpiperidino‐borane 1 reacts with nitriles not in a [2 + 2] cycloaddition manner but to form azaborafluoranthenes 3 whose BNC 4 ring shows a C–B–N–C element reminiscent to a butadiene unit as revealed by an X‐ray structure analysis of 3a . An unexpected 3:1 reaction occurs between tert ‐butyl isonitrile and 1 leading to the keteneimino azaborolidine 10 . Its central ring shows an envelope conformation. 1 is fairly inert towards olefins. Out of 5 examples only 1,1‐diethoxyethene gave the [2 + 2] cycloaddition product, i.e. the boretane 4 .