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. 2015 Jul 29;11:1274–1331. doi: 10.3762/bjoc.11.142

Scheme 69.

Scheme 69

Synthesis of metacyclophane via Cope rearrangement. Reagents and conditions: (i) MeOH, NaBH4, rt, 1 h, 95%; (ii) PBr3, C6H5CH3, Et2O, 12 h, 60 °C, 96%; (iii) Na2S, C6H6, EtOH, Cs2CO3, 8 h, 80 °C, 51%.