Search results

Search for "thermal [3,3]-sigmatropic rearrangement" in Full Text gives 3 result(s) in Beilstein Journal of Organic Chemistry.

Sequential Diels–Alder/[3,3]-sigmatropic rearrangement reactions of β-nitrostyrene with 3-methyl-1,3-pentadiene

  • Peter A. Wade,
  • Alma Pipic,
  • Matthias Zeller and
  • Panagiota Tsetsakos

Beilstein J. Org. Chem. 2013, 9, 2137–2146, doi:10.3762/bjoc.9.251

Graphical Abstract
  • . Epimerization occurred at C-6 (the C-atom attached to the nitronate O-atom). An intermediate cyclic zwitterion would seem to be present and is consistent with observed relative rates of isomerization. The rate (and success) of the thermal [3,3]-sigmatropic rearrangement of O-allyl nitronic esters appears to
PDF
Album
Supp Info
Full Research Paper
Published 17 Oct 2013

Recent advances in carbocupration of α-heterosubstituted alkynes

  • Ahmad Basheer and
  • Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

Graphical Abstract
  • undergoes a subsequent thermal [3,3]-sigmatropic rearrangement to give the corresponding nitrile 27. The presence of the organomagnesium group on 26 is essential for the rearrangement to proceed in good yield (Scheme 12). The silylcupration of N-1-alkynylsulfonylamides 28 led to the desired vinylsilane
PDF
Album
Review
Published 15 Jul 2010

A thermally-induced, tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition approach to carbocyclic spirooxindoles

  • Kay M. Brummond and
  • Joshua M. Osbourn

Beilstein J. Org. Chem. 2010, 6, No. 33, doi:10.3762/bjoc.6.33

Graphical Abstract
  • observed, but are likely intermediates of an infrequently encountered thermal [3,3]-sigmatropic rearrangement of a propargylic acetate. Keywords: allene; propargylic acetate; spirooxindole; thermal [2 + 2] cycloaddition; thermal [3,3]-sigmatropic rearrangement; vinylidene indolin-2-one; Introduction
  • 5 could be obtained by way of a thermal [3,3]-sigmatropic rearrangement of the propargylic acetate 6 to give compound 5 where R2 = OAc (Figure 2) [27]. Preparation of propargylic acetate 9a was accomplished by the addition of the lithium acetylide of 8 to N-methyl isatin (7) followed by acetylation
  • allenyl acetate in intermediate 11 which in turn arises from the thermal [3,3]-sigmatropic rearrangement of 9a (Figure 3). We have briefly investigated the scope and limitations of this tandem cycloaddition reaction by varying the protecting group on the oxindole nitrogen, altering the substitution on the
PDF
Album
Supp Info
Preliminary Communication
Published 08 Apr 2010
Other Beilstein-Institut Open Science Activities