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Isomere Aminoborane und Amin‐Borane mit cis ‐BC CSi‐Gruppierung — Herstellung und Charakterisierung
Author(s) -
Könter Roland,
Seidel Günter,
Wrackmeyer Bernd
Publication year - 1990
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.19901231210
Subject(s) - chemistry , boranes , stereochemistry , borane , medicinal chemistry , bicyclic molecule , amine gas treating , catalysis , organic chemistry , boron
Isomeric Aminoboranes and Amine‐Boranes with cis ‐BC CSi Groupings — Preparation and Characterisation The reaction of the heterocycles ) [R 3 CH 3 : A; R 3 C(CH 3 ): CH 2 : B] with the prim.‐aminohydroxyalkanes H 2 NROH [R CH 2 CH 2 : 1 ; CH(C 2 H 5 )CH 2 : rac ‐ 2 , R ‐ 2 ,; [CH 2 ] 3 : 3 ; [CH 2 ] 4 : 4 ], the prim‐aminophenols H 2 NC 6 H 4 OH [ ortho ; 5 ; meta : 6 ], and the sec.‐aminohydroxyalkanes HN(CH 3 ) ROH [R [CH 2 ] 2 : 7 ; ( R,S )‐CH(CH 3 )CH(C 6 H 5 ) : 8 ; ( S,S )‐CH(CH) 3 )CH(C 6 H 5 ): 9 ] leads to elimination of CH 3 NH 2 with formation of the compounds 11a, b, 12–15 and 17–19 as monocyclic aminoboranes B(C 2 H 5 ) (R 1 H, CH 3 ; R 3 CH 3 ) and iso ‐ 11a,b , iso ‐ 12 ‐ iso ‐ 15 as bicyclic amine‐boranes . The isomeric compounds 11a and iso ‐ 11a are transformed into one another by crystallisation and by dissolution or distillation, resp. A reacts with the tert.‐aminoethanol (CH 3 ) 2 NCH 2 CH 2 OH ( 10 ) to give the acyclic compound (CH 3 ) 2 N(CH 2 ) 2 OSi(CH 3 ) 2 C(CH 3 C(C 2 H 5 )B(C 2 H 5 )O(CH 2 ) 2 ‐N(CH 3 ) 2 ( 20 ). Further reactions of A with the NH 2 compounds HN(CH 3 )[CH 2 ] 2 NH 2 ( 21 ), CH 3 C(O)NH 2 , and NCNH 2 to the compounds E, 23 , and 24 , resp., are described. — The compounds ( i 1 ) and cis ‐HC(C 2 H 5 ) C(CH 3 )Si(CH 3 ) 2 ORNH 2 ( i 2 ) are formed as side products by BC(vinyl) fission.