Synthesen mit Dichlorvinylencarbonat als Dieno‐ und Photocyclophil

Scharf, Hans‐Dieter; Droste, W.; Liebig, R.

doi:10.1002/ange.19680800512

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1970

1974

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Cited by 34 publications

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“…Contraction of the four-membered ring in the bicyclic compound (68) and rearrangement of the resulting cyclopropanol system (69) are accepted as characteristic reaction steps.…”

Section: With Carbanionsmentioning

confidence: 99%

“…The products are azabicyclo[4.1.0]heptenes (77) [661, which rearrange smoothly in alkaline media to give the 3-hydroxypyridones (78) [671. It may be assumed that the bicyclic compound (76) heteroanalogous to (68) is formed via the cyclobutane-1,2-dione stage ( 7 5 ) ; ring contraction then leads to (77). Similar ring contractions have been known in the cyclobutane-I ,2dione series for some time[68J.…”

Section: With Enaminesmentioning

confidence: 99%

See 1 more Smart Citation

The Chemistry of Phenylcyclobutenediones

Ried¹,

Schmidt²

1972

Angew. Chem. Int. Ed. Engl.

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Phenylcyclobutenediones are easily obtainable and very stable. Depending on the nature of the substituent R in position 3, they may be formally regarded as vinylogous carboxylic acid derivatives (Rhalogen, OCH3, OH, SH) or as α,β‐unsaturated diketo compounds (RH, alkyl, aryl). Their behavior in reactions justifies this approach. Ring contraction, ring expansion, and ring cleavage reactions are described.

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“…Contraction of the four-membered ring in the bicyclic compound (68) and rearrangement of the resulting cyclopropanol system (69) are accepted as characteristic reaction steps.…”

Section: With Carbanionsmentioning

confidence: 99%

Section: With Enaminesmentioning

confidence: 99%