Details
| Original language | English |
|---|---|
| Pages (from-to) | 2385-2390 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 14 |
| Publication status | Published - 1 Jul 2002 |
Abstract
1,3-Bis(ethylenedioxy)-2-indanone (2) was shown to react with some dienophiles to give naphthoquinone acetals under photochemical reaction conditions, presumably by photodecarbonylation via the corresponding ortho-quinodimethane. With maleic anhydride the highly oxygenated benzocycloheptane derivative rac-12 was obtained in good yield. In a similar manner, upon irradiation in the presence of acrylonitrile a 2:1 mixture of ring-expanded regioisomers rac-13 and rac-14 was obtained. Irradiation in the presence of fumarodinitrile unexpectedly gave the spirocyclic compound rac-15, which was characterized by X-ray crystallography, rac-15 is the trapping product of oxacarbene 16, thus demonstrating a rare case of a ring expansion of a cyclopentanone to give a six-membered ring oxacarbene, here leading to an orthoester.
Keywords
- Carbenes, Ninhydrin, Oxygen heterocycles, Photochemistry, Ring expansion
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, No. 14, 01.07.2002, p. 2385-2390.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Ninhydrin as a source of naphthoquinone acetals and benzocycloheptenetrione derivatives, and the trapping of an oxacarbene derived from a cyclopentanone
AU - Leinweber, Dirk
AU - Schnebel, Matthias
AU - Wartchow, Rudolf
AU - Wey, Hans Günther
AU - Butenschön, Holger
PY - 2002/7/1
Y1 - 2002/7/1
N2 - 1,3-Bis(ethylenedioxy)-2-indanone (2) was shown to react with some dienophiles to give naphthoquinone acetals under photochemical reaction conditions, presumably by photodecarbonylation via the corresponding ortho-quinodimethane. With maleic anhydride the highly oxygenated benzocycloheptane derivative rac-12 was obtained in good yield. In a similar manner, upon irradiation in the presence of acrylonitrile a 2:1 mixture of ring-expanded regioisomers rac-13 and rac-14 was obtained. Irradiation in the presence of fumarodinitrile unexpectedly gave the spirocyclic compound rac-15, which was characterized by X-ray crystallography, rac-15 is the trapping product of oxacarbene 16, thus demonstrating a rare case of a ring expansion of a cyclopentanone to give a six-membered ring oxacarbene, here leading to an orthoester.
AB - 1,3-Bis(ethylenedioxy)-2-indanone (2) was shown to react with some dienophiles to give naphthoquinone acetals under photochemical reaction conditions, presumably by photodecarbonylation via the corresponding ortho-quinodimethane. With maleic anhydride the highly oxygenated benzocycloheptane derivative rac-12 was obtained in good yield. In a similar manner, upon irradiation in the presence of acrylonitrile a 2:1 mixture of ring-expanded regioisomers rac-13 and rac-14 was obtained. Irradiation in the presence of fumarodinitrile unexpectedly gave the spirocyclic compound rac-15, which was characterized by X-ray crystallography, rac-15 is the trapping product of oxacarbene 16, thus demonstrating a rare case of a ring expansion of a cyclopentanone to give a six-membered ring oxacarbene, here leading to an orthoester.
KW - Carbenes
KW - Ninhydrin
KW - Oxygen heterocycles
KW - Photochemistry
KW - Ring expansion
UR - http://www.scopus.com/inward/record.url?scp=0036063866&partnerID=8YFLogxK
U2 - 10.1002/1099-0690(200207)2002:14<2385::AID-EJOC2385>3.0.CO;2-S
DO - 10.1002/1099-0690(200207)2002:14<2385::AID-EJOC2385>3.0.CO;2-S
M3 - Article
AN - SCOPUS:0036063866
SP - 2385
EP - 2390
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 14
ER -