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3‐Borolene mit diastereotopen Seiten: Synthese von 4‐(Dialkylamino)‐4‐boratricyclo[5.2.1.0 2,6 ]dec‐2(6)‐enen und Struktur des Dimethylamino‐Derivats
Author(s) -
Herberich Gerhard E.,
Spaniol Thomas P.,
Steffan Uwe
Publication year - 1994
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.19941270813
Subject(s) - chemistry , stereochemistry , boranes , derivative (finance) , organic chemistry , financial economics , economics , boron
3‐Borolenes with Diastereotopic Faces: Synthesis of 4‐(Dialkylamino)‐4‐boratricyclo[5.2.1.0 2,6 ]dec‐2(6)‐enes and Structure of the Dimethylamino Derivative Two syntheses of 2,5‐dihyro‐1 H ‐borole derivatives with diastereotopic faces are described. 2,3‐Dimethylenenorbornane ( 2 ) is transformed into the zirconocene complex 5 (≡ Cp 2 Zr · 2 ) in a large‐scale preparation; 5 reacts with dichloro‐(dialkylamino)boranes BCl 2 (NR 2 ) to give 4‐(dialkylamino)‐4‐boratricyclo[5.2.1.0 2,6 ]dec‐2(6)‐enes 1 (R = Me, i Pr). Alternatively, 2,3‐dimethylnorbornene (santene) ( 3 ) or 3‐methyl‐2‐methylenenorbornane ( 4 ) can be kaliated by means of Lochmann‐Schlosser base to give a dimetallation product 6 (≡ K 2 2 ); treatment of 6 with BCl 2 (NR 2 ) also affords the boratricycles 1 (R = Et, i Pr). The structure of the dimethylamino derivative 1a has been determined by X‐ray diffraction.