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Synthese von tricyclischen 2,3‐Dihydro‐1 H ‐1,3‐stannaborolen
Author(s) -
Kerschl Susanna,
Wrackmeyer Bernd
Publication year - 1988
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.19881210817
Subject(s) - chemistry , intramolecular force , diethylamine , tricyclic , alkyl , amine gas treating , stereochemistry , medicinal chemistry , group (periodic table) , organic chemistry
Synthesis of Tricyclic 2,3‐Dihydro‐1 H ‐1,3‐stannaboroles A weak intramolecular interaction between a strongly basic amino group (SnNEt 2 ) and a trigonal atom suffices to deprotonate a BCH group and to eliminate amine. This is shown by organoboration of (diethylamino)dimethyl‐1‐propynylstannane ( 1 ) using 9‐alkyl‐9‐borabicyclo[3.3.1]nonanes [alkyl Me ( 5a ), Et ( 5b ), i Pr ( 5c )]. In the first step, the heterocycles 6a, b are formed. These eliminate diethylamine upon heating to give the new tricyclic 2,3‐dihydro‐1 H ‐1,3‐stannaborole derivatives 7a, b . In the case of 7c , the intermediate 6c was not observed. 1 H‐, 11 B‐, 13 C‐, and 119 Sn‐NMR data are reported.