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Trimethylsilylierte 1,4‐Diborinane und 1,3‐Diborolane ‐ Bildung, Isomeren‐Trennung und Charakterisierung
Author(s) -
Köster Roland,
Seidel Günter,
Lutz Frank,
Krüger Carl,
Kehr Gerald,
Wrackmeyer Bernd
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.19941270504
Subject(s) - chemistry , trimethylsilyl , adduct , yield (engineering) , diastereomer , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy
Trimethylsilylated 1,4‐Diborinanes and 1,3‐Diborolanes – Formation, Isomer Separation, and Characterisation Me 3 SiCCH (A) reacts with excess (Et 2 BH) 2 via the compounds 1, 1′ and 2, 2′ to yield a mixture of four regio‐ and stereoisomeric 1,4‐diethyl‐2,5(6)‐bis(trimethylsilyl)‐1,4‐diborinanes ( 3a–d ) and minor amounts of 1,3‐diethyl‐2‐methyltrans‐2,5‐bis(trimethylsilyl)‐1,3‐diborolane ( 4a ). The 2, 5‐ee ‐(Me 3 Si) 2 compound 3d is isolated as the adduct 3d (Pic) 2 (X‐ray structure analysis), from which pure 3d is obtained with Et 2 O‐BF 3 . 3d and Me 3 P form equilibria of the 1:1 and 1:2 addition compounds 3d (Me 3 P) n ( n = 1,2) at room temperature. Me 3 SiCCMe ( B ) reacts with (Et 2 BH) 2 via 5 to give 6–10 , and Me 3 SiCCSiMe 3 ( C ) reacts with (Et 2 BH) 2 to form the ring compounds 12 and 13 via the presumably threo / erythro mixture of 11a and b.