Vierringsynthesen durch photosensibilisierte symmetrische und gemischte Cyclo‐Additionen

Schenck, Günther O.; Hartmann, Willy; Mannsfeld, Sven‐Peter; Metzner, Wolfgang; Krauch, Carl Heinrich

doi:10.1002/cber.19620950711

Cited by 104 publications

(27 citation statements)

References 14 publications

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“…From the reaction of 2-vinylpyridine (lb) with N-alkyl-rnaleinimides (2) the 1 : 2-addition products 9 can be isolated in thc presence of polymcrization inhibitors, which are derivatives of N-alkyl-5,6,7,8-tctrnhydrocluinolinc-~, 6-dicarboxirnicles (9). This agsin corrcsponds to the reaction typc of cycloacltiitions with styrcnc.…”

Section: Neuartige Cycloadditionsreaktionen Von 2-und 4-mentioning

confidence: 99%

“…Ausbeute 3 Mol N-Alkyl-maleinimide (2 a-f). Die im Schema 1 angegebene Strukturformel4l) 2', 9', 10'-tetmcarhox)~lic If, Z',9',K,N',S',9',TO'n, \ R der erhaltenen Additionsprodukte griindet sich auf die Massen-und lH-NMK.-Spektren.…”

Section: Neuartige Cycloadditionsreaktionen Von 2-und 4-unclassified

“…C 82,15 H 8,27 N 9,58y0 Gef. ,, 82,31 ,, 8,32 ,, 9,36% B : C,,H,,N, [9]. Das mit 6f isomerc N, N'-l~iphenyl-c~-clobutan~tctracarbons~ure-i~nicl schmilzt bei 342" [9].…”

Section: )unclassified

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Neuartige Cycloadditionsreaktionen von 2‐ und 4‐Vinylpyridin mit N‐Alkyl‐maleinimiden

Wagner‐Jauregg

Ahmed

Pretsch

1973

Helvetica Chimica Acta

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(13. XI. 72) Sumnnzary. 4-Vjnylpyridine (la) combines with 3 moles of dienophilic N-alkyl-maleinimides (2) in the presence of polyrncrization inhibitors. The first stcp of the reaction probably consists of 1 : 1-addition with participation of an aromatic double bond, compa.rablc to the analogous bchavior of styrene and its derivatives undcr similar conditions. The unstable intermediates 3, like other Schzffbascs (imincs), add 2 further molcs of the N-alkyl-malcinimides forming thc spiro compounds 4. These are split in an acidic medium into the N-allryl-5,6,7,8~tetraliydroisoquinoline-7,8-dicarboximidcs (5). and N, N'-dialkyl-2-butcne-1, 2,3,4-tetracarboxylic 1,2, : 3,4-diimides (6). LiAIH,-reduction of thcse two types of compounds leads to N-alkyl-l11-(3,4-d)-pyrrolo-2, 3,3 a,4,5,9b-hexahydroisoquinolines (7) and t o N, N'-dialkyl-3,3'-L1ipyrrolidyls (8A) and their dehy dro-products 8B, respcctively.From the reaction of 2-vinylpyridine (lb) with N-alkyl-rnaleinimides (2) the 1 : 2-addition products 9 can be isolated in thc presence of polymcrization inhibitors, which are derivatives of N-alkyl-5,6,7,8-tctrnhydrocluinolinc-~, 6-dicarboxirnicles (9). This agsin corrcsponds to the reaction typc of cycloacltiitions with styrcnc. Furthermore 1 : 3 adducts are formed which according to ly have the structure 10, representing a new type of cycloaddition

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Section: Neuartige Cycloadditionsreaktionen Von 2-und 4-mentioning

confidence: 99%

Section: Neuartige Cycloadditionsreaktionen Von 2-und 4-unclassified

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Neuartige Cycloadditionsreaktionen von 2‐ und 4‐Vinylpyridin mit N‐Alkyl‐maleinimiden

Wagner‐Jauregg

Ahmed

Pretsch

1973

Helvetica Chimica Acta

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“…For example, on sensitized photolysis, with light absorbed by acetophenone or Michler's ketone, the cis-nnti-cis cyclobutane dimer (1)(2)(3)(4), with head-to-head orientation (4) is formed in 11igh yield. However, on direct irradiation in wllicl~ the light is absorbed by indene, extensive polymerization occurs.…”

Section: Introductionmentioning

confidence: 99%

“…However, on direct irradiation in wllicl~ the light is absorbed by indene, extensive polymerization occurs. Cyclobuta~les can also be obtained by sensitized cross-addition reactions of indene with counlarin (1,4) or acrylonitrile (5). Photolysis of indene and acrylonitrile with no sensitizer results in the forination of 2-(1-indeny1)-propionitrile as the major product (5).…”

Section: Introductionmentioning

confidence: 99%

Photochemical rearrangement and dimerization of 1,1-disubstituted indenes

McCullough¹

1968

Can. J. Chem.

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The pliotochemical behavior of 1,l-diphenylindene and 1,l-dimethylindene has been studied. The fornicr undergoes efficient rearrangement on direct irradiation or on acetophenone sensitization, forming 2,3-diphenylindene and 1 ,Zdiphenylindene. In contrast, 1,l-dimethylindene gave n o detectable products of methyl migration but formed dimeric cyclobutanes on scnsitized and direct photolysis. The structures of thc two dimers formed in the sensitized reaction were assigned from their nuclear magnetic resonance spectra. It was also demonstrated that hydrogen, like methyl, migrated inefficiently if at all in this system. This difference in migrato~y aptitudes is discussed in terms of orbital symmetry of the indene system.

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The synthesis and X-ray structure of 1,2,3,4-cyclobutane tetracarboxylic dianhydride and the preparation of a new type of polyimide showing excellent transparency and heat resistance

Suzuki

Abe

Takaishi

et al. 2000

J. Polym. Sci. A Polym. Chem.

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Some polyimide films based on cyclobutane‐1,2,3,4‐tetracarboxylic dianhydride (CBDA) and aromatic diamines were synthesized to investigate their temperature resistance and percent transmission of light. The preparations of CBDA were investigated; they produced almost 10 times the yield of CBDA in comparison to yields obtained by previous methods. The configuration of CBDA was determined by X‐ray analysis to be cis–trans–cis. The polymer films showed excellent thermal resistance and were transparent and colorless, desirable characteristics for practical applications in the field of polymer engineering. However, the polymer obtained from a pyromellitic dianhydride instead of from CBDA was deep yellow and not desirable for high‐qualified display materials such as liquid‐crystal displays. The percent transmission of the polymers obtained from CBDA and aromatic diamines ranged from 81.5 to 85.8%, whereas the deep‐yellow polymers showed low percent transmissions ranging from 48 to 63.9%. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 108–116, 2000

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Vierringsynthesen durch photosensibilisierte symmetrische und gemischte Cyclo‐Additionen

Cited by 104 publications

References 14 publications

Neuartige Cycloadditionsreaktionen von 2‐ und 4‐Vinylpyridin mit N‐Alkyl‐maleinimiden

Neuartige Cycloadditionsreaktionen von 2‐ und 4‐Vinylpyridin mit N‐Alkyl‐maleinimiden

Photochemical rearrangement and dimerization of 1,1-disubstituted indenes

The synthesis and X-ray structure of 1,2,3,4-cyclobutane tetracarboxylic dianhydride and the preparation of a new type of polyimide showing excellent transparency and heat resistance

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