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Extra info for Advanced Problems in Organic Reaction Mechanisms
Give a mechanistic interpretation for this transformation which takes into account the probable role of the solvent. O Me Me Me Me O 1 Advanced Problems in Organic Reaction Mechanisms 39. 21 Benzopyrene Synthesis- By Accident During studies on the synthesis of trihydroxybenzopyrene derivatives it was found that treatment of the pentacycle 1 with HI/50% H3PO2 at 100~ for 2 to 3 minutes resulted in smooth conversion into the trimethoxybenzopyrene 2 in 95% yield. Suggest a mechanism for this transformation.
Photochemical Rearrangement of Pyran-2-ones The photochemical behaviour of pyran-2-ones continues to attract interest and to yield unusual types of reaction. In a recent example it was found that irradiation of the 6-(2hydroxyalkyl)pyran-2-ones 1 in methanol under carefully optimised conditions (which were not 50 Advanced Problems in Organic Reaction Mechanisms clearly specified) gave a diastereomeric mixture of solvent adducts. Removal of the solvent and treatment of the residue with a catalytic amount of HC1 in THF at room temperature resulted in formation of the dihydropyrans 2 in good yield.
Benzodiazepines from (R)-(+)-Pulegone (R)-(+)-Pulegone 1, a major constituent of the essential oils of Mentha species, is a cheap, readily available and valuable synthetic precursor from the chiral pool. When a solution of equimolar amounts of 1 and o-phenylenediamine in toluene was heated at reflux for 4 days, the tricyclic benzodiazepine derivative 2 was obtained in 68% yield. 5-Methyl- and 5-chloro-ophenylenediamine reacted similarly to give the analogous benzodiazepines in 70 and 60% yield respectively.