Trinacrene (1) is a promising—and very attractive‐new cage compound with a name derived from an old designation for Sicily (Trinacrien). The synthesis of 1 was accomplished in two steps involving six (2 × 3) Diels–Alder reactions and highly symmetrical precursors, the second step being a high‐pressure reaction (10 kbar). Compound 1 displays D3h symmetry and gives only the predicted five 1H NMR signals.
The synthesis of 2-acetoacetyl-5-benzoyl-1 -phenylpyrrolidin-3-one (5) from diketen and C-benzoyl-N-phenylazomethine oxide (benzoylmethyleneaniline N-oxide) is described. Its structure was elucidated by spectrometric methods, and its main mass spectral fragmentation path is presented. The formation of product ( 5) by a cycloaddition reaction followed by intramolecular rearrangement and acetoacetylation is discussed.
Electrophilic brornination of the isoxazole ring proceeds via a stabilized isoxazoliurn ion, which can undergo an i n t ra m o I e c u I a r cis-ad d it i o n of a n ei g h b o u r i n g be nza rn i d oor c a r b o x y I ate g r o u p to afford b r o m o s p i ro b ih e t e r o c y c i i c compounds containing the isoxazoline ring, or rearrangement products.
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