σ, π‐Isomerisierungen von Monohetero‐σ‐bishomobenzol‐Derivaten. Vorläufige Mitteilung

Stusche, Dieter; Breuninger, Manfred; Prinzbach, Horst

doi:10.1002/hlca.19720550710

Cited by 27 publications

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References 18 publications

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“…The preparation of cis-monohetero-bis-and -tris-homobenzene derivatives, ( I ) and (3), respectively, has been reported several times"]. These systems are not of the least preparative importance because of the o+x isomerization to (2) and (41, respectively.…”

Section: Cis-trioxatris-o-homobenzene (And-"benzenementioning

confidence: 99%

cis‐Trioxatris‐σ‐homobenzene (cis‐“Benzene Trioxide”)

Schwesinger

Prinzbach

1972

Angew. Chem. Int. Ed. Engl.

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by the formation of (11) and (12), the norcaradienediester (3c) which is not directly detectable can be trapped by diazomethane in the carbocyclic system (2c) $ (3c). However, it appears that addition of CH2N, to (3c) and to (11) occurs, even if not exclusively, in a manner with high selectivity trans to the cyclopropane ring. The cis-selectivity found for (3a), (3b), (4a), and ( 4 b ) must consequently be ascribed to a cis-directing effect of the hetero ring members"]. Carbocyclic cis-o-trishomobenzene derivatives thus seem to be inaccessible by the ( I ) -(6) route ['].The structures of the new compounds have been proved by subsequent reactions, elemental analyses and spectroscopic data (Table 1). The coupling constants determined shift could not be avoided; after hydrolysis of the ester mixture [a. 60% of (Zc) with ca. 30% of dimethyl cycloheptatriene-1,7-dicarhoxylate (Ze) and 8% of dimethyl cycloheptatriene-2,3-dicarboxylate (Zf)].

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Section: Cis-trioxatris-o-homobenzene (And-"benzenementioning

confidence: 99%