45 °C for 0.5 h. Sodium hydride (0.25 mmol) (10 mg of 60% NaH dispersed in mineral oil washed with petroleum ether) was added to the solution. After cessation of gas evolution 0.5 mL of 5% DC1 was added. TLC on silica gel (9% MeOH in CH2C12, UV visualization) showed only the ring-contracted product 3 had formed; this was confirmed by proton NMR on the reaction mixture.Acknowledgment. We thank E. Reich for elemental analyses, M. Mentzer for mass spectral data, and D. Staiger and G. Zuber for some of the NMR data. We acknowlede the encouragement of Dr. G. Dunn.
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