Synthesis, structure, and reactivity of secosteroids containing a medium‐sized ring. Part 32 . Conformations and photochemical reactivity of some unsaturated 5,10‐secosteroidal ketones | Zendy

Lorenc Ljubinka | Zendy; Pavlović Vladimir | Zendy; Mihailović Mihailo Lj. | Zendy; Kalvoda Jaroslav | Zendy; Fuhrer Hermann | Zendy

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Synthesis, structure, and reactivity of secosteroids containing a medium‐sized ring. Part 32 . Conformations and photochemical reactivity of some unsaturated 5,10‐secosteroidal ketones

Author(s) -

Lorenc Ljubinka,

Pavlović Vladimir,

Mihailović Mihailo Lj.,

Kalvoda Jaroslav,

Fuhrer Hermann

Publication year - 1991

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19910740709

Subject(s) - chemistry , intramolecular force , reactivity (psychology) , ring (chemistry) , ketone , stereochemistry , photochemistry , intramolecular reaction , ground state , medicinal chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics

UV irradiation of the unsaturated ( E )‐5,10‐secosteroidal ketones 1 and 6 results, in addition to ( E / Z )‐isomeri‐zation, in an intramolecular Pateino‐Büchi reaction and, in the case of 1 , in transannular cyclization (along with AcOH elimination). The stereochemistry of the observed intramolecular photoprocesses can be explained in terms of ground‐state conformations of the ( E )‐seco‐ketones 1 and 6 in solution.

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