Crystal and molecular structure of 14c-hydro-5a-phenylbenz[a]indeno[2,1-c]fluorene-5,10-dione

Bednowitz, A. L.; Hamilton, Walter C.; Brown, R. K.; Donaruma, Lorraine G.; Southwick, Philip L.; Kropf, Ronald A.; Stanfield, R. A.

doi:10.1021/ja01004a015

Cited by 4 publications

(1 citation statement)

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“…On the other hand, the reaction of cis ‐PhCH=CPhC(=O)Cl with NbCl 5 revealed poorly selective, affording a mixture of products among which 2 and 4 were identified (ESI‐MS, 1 H NMR), see Scheme e. Compound 4 ( phenylcinnamalone ) and substituted derivatives were obtained in the past from cis ‐PhCH=CPhC(=O)Cl only under solventless, harsh conditions (T ≥ 160 °C) ,…”

Section: Resultsmentioning

confidence: 99%

Cascade Reactions of α‐Phenylcinnamic Acid to Polycyclic Compounds Promoted by High Valent Transition Metal Halides

et al. 2018

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α‐Phenylcinnamic acid converts into polycyclic derivatives by interaction with high valent transition metal halides in chloroform at reflux temperature. Different products, featured by local structural differences depending on the nature of the metal halide system (i. e. WCl6, PCl5/NbF5 or PCl5/NbCl5), are easily isolable after treatment with water. In particular, WCl6 configures as an efficient multitasking agent, working as 1) chlorinator of the carboxylic acid function, 2) catalytic precursor for intra‐ and intermolecular rearrangements, and 3) catalytic precursor for Baeyer‐Villiger lactonization in water at ambient temperature, exploiting air as oxidant. The products have been purified by alumina chromatography, and identified by analytical and spectroscopic (IR, NMR) techniques, and by single crystal X‐ray diffraction in three cases. Their formation probably involves a common reaction pathway which has been rationalized by DFT calculations.

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Section: Resultsmentioning

confidence: 99%