Chemistry of Heterocyclic Compounds: Seven-Membered by Andre Rosowsky

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By Andre Rosowsky

Content material:
Chapter I Oxepins and diminished Oxepins (pages 1–50): Andre Rosowsky
Chapter II Oxepin Ring platforms Containing jewelry (pages 51–135): Andre Rosowsky
Chapter III Oxepin Ring platforms Containing 3 earrings (pages 136–258): Andre Rosowsky
Chapter IV Oxepin Ring structures Containing greater than 3 jewelry (pages 259–318): Andre Rosowsky
Chapter V Dioxepins and Trioxepins (pages 319–411): Chester E. Pawloski
Chapter VI Terpene Oxepins (pages 412–466): A. N. Starratt
Chapter VII Steroidal Oxepins (pages 467–520): John A. Zderic
Chapter VIII Oxepins Derived From Sugars (pages 521–559): T. R. Hollands
Chapter IX Alkaloids Containing a Seven?Membered Oxygen Ring (pages 560–572): Paul J. Scheuer
Chapter X Monocyclic Seven?Membered earrings Containing Sulfur (pages 573–666): Lamar box and David L. Tuleen
Chapter XI Condensed Thiepins (pages 667–896): Vincent J. Traynelis

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Additional resources for Chemistry of Heterocyclic Compounds: Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur, Volume 26

Example text

Treatment of this mixture with N-bromosuccinimide afforded a monoallylic bromide. This intermediate was then dehydrobrominated directly to a dihydrooxepin which may well have been 59, although a firm structure was never actually assigned. ) C- 19 compound 80 t HBS A + 0 81 0 82 The synthesis of 4,5-dihydrooxepin (60) was first reported in 1961 by Pohl (48), who observed the formation of this compound during the pyrolysis (83) at 470". of 2-acetoxy-2,3,4,5-tetrahydrooxepin 83 60 A second method of preparation of 60 was published in 1963 by Braun (5).

C- 19 compound 80 t HBS A + 0 81 0 82 The synthesis of 4,5-dihydrooxepin (60) was first reported in 1961 by Pohl (48), who observed the formation of this compound during the pyrolysis (83) at 470". of 2-acetoxy-2,3,4,5-tetrahydrooxepin 83 60 A second method of preparation of 60 was published in 1963 by Braun (5). Acrolein was converted into 1,5-hexadiene-3,4-dioI (84) in 90 % yield under the influence of a zinc-copper couple. Condensation of 84 with diethyl carbonate then gave synz-divinylethylene carbonate (85) in 74 % yield.

An authentic specimen of 25 was prepared by reduction of 24 with sodium borohydride. No evidence could be found for the presence of 2,7-diphenyloxepin (26) under the conditions studied. When 24 was treated with ethyl diazoacetate in acetonitrile at O", a complex mixture was formed once again, from which a 9 % yield of 25 could be isolated by thin-layer chromatography. The yield of 25 was raised to 14 % upon addition of triethylamine. If the reaction was conducted in the presence of one equivalent of 2,6-lutidine as a proton acceptor, the major product (18%) recoverable from the reaction mixture proved to be 2,6-diphenyl-4-carbethoxymethylene-4H-pyran (27), rather than the hoped-for 4-carbethoxy-2,7diphenyloxepin (28).

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