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Contribution to the Chemistry of Boron, 235. Reactions of Prolinol with Borane–Tetrahydrofuran: Anomalous Dimerization of a 1,3,2‐Oxazaborolidine
Author(s) -
Lang Andreas,
Nöth Heinrich,
Schmidt Martin
Publication year - 1997
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.19971300217
Subject(s) - chemistry , tetrahydrofuran , borane , adduct , boron , medicinal chemistry , hydrogen atom , hydrogen , atom (system on chip) , tetrahedron , product (mathematics) , stereochemistry , photochemistry , crystallography , organic chemistry , catalysis , solvent , alkyl , geometry , mathematics , computer science , embedded system
The reaction of ( S )‐prolinol (LH) with H 3 B · THF proceeds via [L 2 BH 2 <]BH 4 , which decomposes with elimination of hydrogen at ca. −40°C to give the BH 3 adduct of spirocyclic 7 . On heating, 7 loses more H 2 to give the “anomalous” dimerization product 11 , which features a tetracoordinated B atom in a “tetrahedral” BN 2 O 2 unit and another B atom in an N 2 BH 2 environment. It is also shown that the product resulting from the reaction of pseudoephedrin with H 3 B·THF undergoes an analogous anomalous dimerization, affording product 8 .