Skip to Main content Skip to Navigation
Journal articles

Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

Abstract : A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp(2) boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp(3) boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. (1)H and (11)B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence
Document type :
Journal articles
Complete list of metadatas

https://hal-univ-rennes1.archives-ouvertes.fr/hal-01165428
Contributor : Laurent Jonchère <>
Submitted on : Friday, June 19, 2015 - 9:57:12 AM
Last modification on : Thursday, March 5, 2020 - 2:06:59 PM

Links full text

Identifiers

Citation

Ludovic Eberlin, Bertrand Carboni, Andrew Whiting. Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds. Journal of Organic Chemistry, American Chemical Society, 2015, 80 (13), pp.6574-6583. ⟨10.1021/acs.joc.5b00593⟩. ⟨hal-01165428⟩

Share

Metrics

Record views

229