Journal ArticleDOI
Sigmatropische Umlagerungen von Aryl‐propargyläthern; Synthese von 1, 5‐Dimethyl‐6‐methylen‐tricyclo[3, 2, 1, 02,7]‐oct‐3‐en‐8‐on‐Derivaten. Vorläufige Mitteilung
Janos Zsindely,Hans Schmid +1 more
TLDR
This paper showed that the known thermal cyclisation of aryl propargyl ethers to chromenes involves a preliminary [3, 3]-sigmatropic rearrangement.Abstract:
2, 6-Dimethylphenyl propargyl ether (10) and its derivatives 12–15 rearrange thermally to 1, 5-dimethyl-6-methylene-tricyclo [3.2.1.02,7]oct-3-en-8-one (9) and related compounds 16–19. The ethers undergo first an aromatic [3, 3]-sigmatropic rearrangement to ortho-allenyldienones 11, which then undergo ring closure to the tricyclic products by an electrocyclic reaction.
Only in the case of the γ-methylpropargyl ether 13, the ortho-dienone 11 is further rearranged in low yield to the para-butynylphenol 20, but the tricyclic ketone 17 is again the main product.
New data show that the known thermal cyclisation of aryl propargyl ethers to chromenes (e. g. 4 8) involves a preliminary [3, 3]-sigmatropic rearrangement.read more
Citations
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Advances in addition-cure phenolic resins
TL;DR: In this article, the chemistry of addition-cure phenolic resins and the different strategies involved in their molecular design are discussed, and the thermal, physical and mechanical properties are discussed and the structure-property correlations examined.
Journal ArticleDOI
Total Synthesis of the Biscarbazole Alkaloids Murrafoline A–D by a Domino Sonogashira Coupling/Claisen Rearrangement/Electrocyclization Reaction
TL;DR: Aryl-pyran-linked biscarbazole alkaloids of the murrafoline group were accessed readily by a novel domino reaction sequence involving Sonogashira coupling, a Claisen rearrangement, and electrocyclization, and the one-pot procedure enables the straightforward synthesis of these structurally challenging alkal steroids in only a few steps.
Journal ArticleDOI
Intramolecular pericyclic reactions of acetylenic compounds
Journal ArticleDOI
Synthesis and Photochromic Behaviour of Naphthopyrans, Pyranoquinolines, Pyranoquinazolines and Pyranoquinoxalines
TL;DR: In this article, new chromenes annulated with different six-membered azaheterocycles were prepared, i.e., the 3H-pyra-no[3,2-f]quinolines 9/10 and 14, the 8H-pyrano[2,3-h]isoquinoline 11, the 4H-polygonal quaternions 12, the 6H-quaternions 13/14, and the 2H-πarano[1,3]-isopropylnaphthopyr
References
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Journal ArticleDOI
Stereochemistry of Electrocyclic Reactions
Journal ArticleDOI
Selection Rules for Sigmatropic Reactions
Journal ArticleDOI
Reactions of Tetrazines with Unsaturated Compounds. A New Synthesis of Pyridazines
R. A. Carboni,R. V. Lindsey +1 more
Journal ArticleDOI
Bicyclo[1.1.0]butane
K.B. Wiberg,K.B. Wiberg,G.M. Lampman,G.M. Lampman,R.P. Ciula,R.P. Ciula,D.S. Connor,D.S. Connor,P. Schertler,P. Schertler,J. Lavanish,J. Lavanish +11 more
TL;DR: The chemistry of bicyclo[1.1.0] butane and some of its derivatives is reviewed in this paper, where the effect of its bond angle deformation on its strain energy, its orbital hybridization, and its reactivity is discussed.
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