Tetrahydro-oxepine

The single crystal X-ray structure of the enantiopure tetrahydro oxepin-2-one 61, a mimic of steroidal androgens, has been reported <06ZN(B)111>. A new procedure has been described for the synthesis of substituted furano-fused oxepines based on expoxidation of strained fused cyclobutenes followed by thermal rearrangement <06OL5183>. 

Oxepins. - Formation. The tetrahydro-oxepin derivatives (129) and (130), notable as the first heterocyclic rrans-cycloheptenes, have been synthesized via decomposition of the diazonium ion (128). They rearranged slowly to the ds-isomers at room temperature but could readily be trapped as Diels-Alder adducts with 2,3-dimethylbuta-l,3-diene. ... 

The maytolins are an interesting instance of new sesquiterpenes from the Celastraceae characterized by the presence of a tetrahydro-oxepine nucleus. It would seem that these new types of skeleton are only biosynthesized by species of the MORTONIA genus, which consists of just four species, endemic to Mexico and the southern Unites States. The chemical study of three of these four species led to the isolation and characterization of eight new sesquiterpenes [31-33](Figure3). 

Didiloro-2-oxabicydo[4.1.0]heptane added all at once to a soln. of K in /er/-butanol, and refluxed 24 hrs. 3-chloro-2-fer/-butoxy-2,5,6,7-tetrahydro-oxepin (Y 79%) mixed with dioxane and shaken ca. 12 hrs. at room temp, with 2 N HCl 2H-3,4-dihydropyran-5-carboxaldehyde (Y 92%). L. Skatteb0l, J. Org. Chem. 35, 3200 (1970). 

Oxepin, 2-acetoxy-2,3,4,5-tetrahydro-thermal reactions, 7, 559 Oxepin, 3-chloro-synthesis, 3, 725 Oxepin, 2,3-dihydro-cycloaddition reactions, 7, 563 nucleophilic reactions, 7, 562 reduction, 7, 563 Oxepin, 2,5-dihydro-synthesis, 7, 578, 580 Oxepin, 4,5-dihydro-formation, 7, 579 reduction, 7, 563 synthesis, 7, 579 Oxepin, 2,7-dimethyl-NMR, 7, 552... 

Oxepin, 4-ethoxycarbonyl-2,3,6,7-tetrahydro-synthesis, 7, 578 Oxepin, 2-methyl-enthalpy of isomerization, 7, 555 Oxepin, 2,3,4,5-tetrahydro-reduction, 7, 563 synthesis, 7, 578 Oxepin, 2,3,4,7-tetrahydro-synthesis, 7, 578 Oxepin, 2,3,6,7-tetrahydro-oxidation, 7, 563 reduction, 7, 563 Oxepin-2,6-dicarboxylic acid stability, 7, 565 Oxepinium ions synthesis, 7, 559 Oxepins, 7, 547-592 antiaromaticity, 4, 535 applications, 7, 590-591 aromatization, 7, 566 bond lengths and angles, 7, 550, 551 cycloaddition reactions, 7, 27, 569 deoxygenation, 7, 570 dipole moment, 7, 553 disubstituted synthesis, 7, 584... 

O-Alkylation of A-(phenacyl)- and Af-(pivaloylmethyl)-derivatives of A-(benzhydryl>-(2R,3R)-c(.v-2,3-epoxybutyramide gave 4,5,6,7-tetrahydro-4-aza-oxepin-5-ones by Sni reactions under basic conditions <00T3209>. 

Scheme 21 2,3-Dihydrobenzofurans, chromans, and 2,3,4,5-tetrahydro-benzo[6]oxepines by sequential ort/io-alkylation-vinylations [75,76]...

Oxepin 3-Chlor-2-(2-chlor-ethoxy)-2,5,6,7-tetrahydro- E14a/1, 406 (Enol-ether -f- CHX3/Oxiran) Propensaure 3-Chlor-3-ethoxy-2-propyl- -chlorid E15/2, 1600 (In-OR + COCl2)... 

Oxepin 7-Propanoyloxy-4,5,6,7-tetrahydro- VI/4, 485 1,3-Pentadien 4-Ethoxycarbonyl-oxy-2-methyl-E15/l, 14(En-al + Cl COOR)... 

ZaR AR, lS,%aR -Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-l, 3-dioxolo[4,5-c]oxepin-6(4//)-one, Q-10 Tetrahydro-3-hydroxy-5-hydroxymethyl-3-furancarboxylic acid, T-26 2,3,3a, 9a-Tetrahydro-3-hydroxy-6-imino-6/ -furo[2, 3 4,5]oxazolo[3,2-a]-pyrimidine-2-methanol, C-170 Tetrahydro-5-hydroxy-3-methylene-2-furanmethanol, D-629 7,8,9,10-Tetrahydro-8-hydroxy-3-methyl-6,9-epoxy-2ff,6ff-pyrimido[2,l-6]-[l,3]oxazocin-2-one, A-715 Tetrahydro-2-hydroxy-6-methylpyran, H-144 Tetrahydro-2-(hydroxymethyl)pyran, T- ... 

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