Download Chemistry of Heterocyclic Compounds: Seven-Membered by Andre Rosowsky PDF

By Andre Rosowsky

Content material:
Chapter I Oxepins and lowered Oxepins (pages 1–50): Andre Rosowsky
Chapter II Oxepin Ring platforms Containing earrings (pages 51–135): Andre Rosowsky
Chapter III Oxepin Ring structures Containing 3 jewelry (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 jewelry Containing Sulfur (pages 573–666): Lamar box and David L. Tuleen
Chapter XI Condensed Thiepins (pages 667–896): Vincent J. Traynelis

Show description

By Andre Rosowsky

Content material:
Chapter I Oxepins and lowered Oxepins (pages 1–50): Andre Rosowsky
Chapter II Oxepin Ring platforms Containing earrings (pages 51–135): Andre Rosowsky
Chapter III Oxepin Ring structures Containing 3 jewelry (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 jewelry Containing Sulfur (pages 573–666): Lamar box and David L. Tuleen
Chapter XI Condensed Thiepins (pages 667–896): Vincent J. Traynelis

Show description

Read or Download Chemistry of Heterocyclic Compounds: Seven-Membered Heterocyclic Compounds Containing Oxygen and Sulfur, Volume 26 PDF

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

Example text

The lower field signal was assigned to the 2-methyl group in 13, while the higher field signal was assigned to the bridgehead methyl group in the epoxy diene tautomer. The complete coalescence of these peaks at 37” was attributed to the fact that, at this temperature, the rate of interconversion of the two tautomeric forms is very rapid on the nmr time scale. The nmr spectrum of 2,7-dimethyloxepin (17) was analyzed by Vogel and co-workers (24, 65, 66). 19. 75 signal was ascribed to the two ,&protons.

B. Only one example of the synthesis of a substituted hexamethylene oxide derivative by intramolecular cyclization of an open-chain precursor exists in the literature. This consists of the longknown report by Michiels (37) that treatment of 2,7-dimethyl-2,7-octanedien with warm dilute sulfuric acid results in the formation of a product formulated as 2,2,7,7-tetramethyloxepan(134). It seems likely that this reaction is far more general in scope than one isolated example would indicate. The reaction of diazomethane with tetrahydropyran-4-one (135) has been utilized by Maerov (32) and more recently by Olsen and Bredoch (42) for the synthesis of oxepan-4-one (136).

0 mixture of isomeric 7-chloro-7-fluoro-2-oxanorcaranes 73 and 74 was heated at 120" for 3 hr in quinoline, 6-fluoro-2,3-dihydrooxepin (75) was obtained in 77 % yield (based on the amount of 73 consumed), and 74 was recovered unchanged. O mixture of exo-7-fluoro-2-oxanorcarane (76) and endo-7-fluoro-2-oxanorcarane (77) was heated at 120" in quinoline for 10 hr and then at 140" for an additional 5 hr, 59 was obtained, together with some unchanged 76. The concerted disrotatory mechanism proposed by DePuy and co-workers for the isomerization of 70 to 59 was invoked by the Japanese authors for the rearrangement of 73 and 77 as well.

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