Document Detail


Systematic Investigation of the Ring-Expansion Reaction of N-Heterocyclic Carbenes with an Iminoborane Dihydride.
MedLine Citation:
PMID:  24938679     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Conversions of iminoboranes with an N-heterocyclic carbene (NHC) result in borane dihydride formation (BDF) concomitant with dihydrogenated NHC. The iminoborane dihydrides are prone to a hydride-mediated ring-expansion reaction (RER) at elevated temperature, that is, the insertion of the boron atom into the adjacent CN bond of the NHC to yield boracycles. Upon conversion of a saturated-backbone NHC with respective iminoborane precursors RER yet occurs at ambient temperature to yield the ring-expanded products. When a less bulky iminoborane is brought in contact with sterically unhindered NHC neither the iminoborane dihydride is stable at room temperature nor is the RER observed to take place upon heating. The conversions of iminoboranes with very bulky NHC do not show BDF at ambient temperature and only in the case of the less hindered borane precursor the RER is found to proceed in a controlled fashion upon heating.
Authors:
Daniel Franz; Shigeyoshi Inoue
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-6-17
Journal Detail:
Title:  Chemistry, an Asian journal     Volume:  -     ISSN:  1861-471X     ISO Abbreviation:  Chem Asian J     Publication Date:  2014 Jun 
Date Detail:
Created Date:  2014-6-18     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101294643     Medline TA:  Chem Asian J     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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