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Structural Analyses of Borane and Chloroborane Adducts of 1,3,5‐Dithiaza‐, ‐Dioxaza‐, ‐Thiadiaza‐, and ‐Triazacyclohexanes and Their Rearrangement Products, Boracyclohexanes
Author(s) -
FloresParra Angelina,
SánchezRuíz Sonia A.,
GuadarramaPérez Carlos
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199911)1999:11<2063::aid-ejic2063>3.0.co;2-a
Subject(s) - borane , chemistry , adduct , stereocenter , isopropyl , ring (chemistry) , rearrangement reaction , nuclear magnetic resonance spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , catalysis , enantioselective synthesis
Structural and conformational studies performed by 1 H‐, 11 B‐, 13 C‐, two‐dimensional, and variable‐temperature NMR spectroscopy of borane and chloroborane adducts of 1,3,5‐heterocyclohexanes and their rearrangement products, boracyclohexanes, are reported. N ‐Methyl derivatives gave equatorial N ‐borane adducts whereas the N ‐isopropyl derivatives produced the axial borane compounds. Rearrangement reactions of the adducts gave the first examples of chloroboracyclohexanes bearing boron and nitrogen atoms as stable stereogenic centers. BClH 2 and BCl 2 H adducts were found to be more stable towards ring rearrangement than the corresponding N ‐BH 3 analogs.