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Extra resources for Advanced Problems in Organic Reaction Mechanisms
The product, however, was shown to be the ring cleaved compound 3 (71% yield). Suggest a mechanism to explain this transformation. AcQ. O OR3 OAc OH OSiEt3 - 0 OH OCOPh " 1, R 1 = R3 = H; R2 = OH 2, R 1 = C1; R 2 = H; R3 = OAc OCOPh SiEt3 Advanced Problems in Organic Reaction Mechanisms 91. 51 A n Ionic Diels-Alder Reaction In an interesting and potentially very useful extension of the so-called ionic Diels-Alder reaction it was shown that reaction of acetals of the type 1 with various 1,3-dienes 2 in the presence of an acid catalyst followed by hydrolysis with TsOH in methanol gave good yields of cycloadducts 3.
Suggest a mechanism for the conversion of 1 into 2. ~CO2H ~CO2F~ o C1 NCOCHECO2Et C1 1 2 96. An Efficient Chromene Synthesis Lithiation of commercially available phenyl vinyl sulfoxide with LDA followed by reaction with sodium 2-acetyl-4-methylphenoxide gave the expected alcohol in 90% yield. This was not very stable but was nevertheless heated under reflux in ethanolic sodium ethoxide (excess) for 19 hours. Standard work-up and purification gave the chromene 1, also in 90% yield. Give a mechanism for the formation of 1.
2 An I n t r a m o l e c u l a r Ring Closure Treatment of the amide 1 with TFAA in methylene chloride at 25~ gave 2 in 85% yield. Suggest a mechanism for this transformation. Ar SAr I 0 ~ 1 2 Ar = 4-MeC6H4 89. 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.