Umlagerungen anellierter oxanorbornadiene in neue dibenz[b,d]oxepin- und spiro[1H]inden-derivate

Tochtermann, W.; Timm, Heinke; Diekmann, J.

doi:10.1016/s0040-4039(01)83494-8

Cited by 7 publications

(1 citation statement)

References 11 publications

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“…Instead, the benzoxepin 8b and exocyclic ketone 9b were obtained. Earlier photochemical experiments on 7-oxanorbornadienes revealed that such systems undergo formal intramolecular photochemical [2+2] cycloadditions to the corresponding oxaquadricyclanes, followed by thermal isomerization to oxepins via carbonyl ylides . A similar process is shown in Scheme , where the photoisomerization of 4b via oxaquadricyclane 18b and ylide 19b affords the observed product 8b .…”

Section: Resultsmentioning

confidence: 83%

Rearrangements of the Diels−Alder Cycloadducts Obtained from Acetylenic Sulfones and 1,3-Diphenylisobenzofuran

2006

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1,3-Diphenylisobenzofuran afforded Diels-Alder cycloadducts 4a,b with n-butyl- and phenyl-substituted acetylenic sulfones 3a,b, respectively. The products underwent various types of rearrangements under pyrolytic, acid-catalyzed, and photochemical conditions. In the presence of acid, or upon heating in xylenes, they afforded the ketones 5a,b. In addition, the dehydration product 7a was produced from the pyrolysis of 4a, and the unexpected transposed ketone 6b was generated under acid-catalyzed or pyrolytic conditions from 4b via a postulated epoxide intermediate. The photolysis of 4a afforded ketone 5a as the sole isolated product, whereas 5b afforded oxepin 8b and indenyl phenyl ketone 9b. The formation of the latter two products can be rationalized by a series of pericyclic reactions. These include an intramolecular [2+2] cycloaddition, followed by a 1,3-dipolar cycloreversion, for the transformation of 4b to 8b and a series of electrocyclic and [1,3]sigmatropic reactions to convert 8b into 9b.

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Section: Resultsmentioning

confidence: 83%

Rearrangements of the Diels−Alder Cycloadducts Obtained from Acetylenic Sulfones and 1,3-Diphenylisobenzofuran

2006

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Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

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Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

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ChemInform Abstract: POLYCYCLIC COMPOUNDS. PART XI. REARRANGEMENTS OF ANNULATED OXANORBORNADIENES TO NEW DIBENZ(B,D)OXEPINE AND SPIRO(1H)INDENE DERIVATIVES

Tochtermann¹,

Timm²,

Diekmann³

1978

Chemischer Informationsdienst

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Umlagerungen anellierter oxanorbornadiene in neue dibenz[b,d]oxepin- und spiro[1H]inden-derivate

Cited by 7 publications

References 11 publications

Rearrangements of the Diels−Alder Cycloadducts Obtained from Acetylenic Sulfones and 1,3-Diphenylisobenzofuran

Rearrangements of the Diels−Alder Cycloadducts Obtained from Acetylenic Sulfones and 1,3-Diphenylisobenzofuran

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

ChemInform Abstract: POLYCYCLIC COMPOUNDS. PART XI. REARRANGEMENTS OF ANNULATED OXANORBORNADIENES TO NEW DIBENZ(B,D)OXEPINE AND SPIRO(1H)INDENE DERIVATIVES

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