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Beilstein J. Org. Chem. 2016, 12, 260–270, doi:10.3762/bjoc.12.28
Graphical Abstract
Scheme 1: Lewis acid-catalyzed [1,4]-H transfer/1,5-electrocyclization tandem processes of benzylidenemalonat...
Scheme 2: Preparation of benz[f]indenes 5 and 6. Reagents and conditions: i) cyclopentadiene, pyrrolidine, an...
Scheme 3: Postulated reaction path for the conversion 3a → 5a + 6a initiated by a [1,4]-hydride shift.
Scheme 4: Alternative mechanistic paths for the conversion 3a → 5a + 6a initiated by [1,5]-, [1,7]- or [1,9]-...
Scheme 5: Postulated outcome of the conversion 14 → 18 + 19 initiated by a [1,4]-deuteride shift.
Scheme 6: Preparation of deuterated benz[f]indenes 18 + 19 and 21 + 22. Reagents and conditions: i) DMSO, mic...
Scheme 7: Reagents and conditions: i) triethylamine (10%), DMSO, rt, 2 h.
Scheme 8: Preparation of benz[f]indenes 25 and 26. Reagents and conditions: i) cyclopentadiene, pyrrolidine, ...
Scheme 9: Mechanistic paths for the conversion of fulvene 3a into the benz[f]indenes 5a and 6a showing the en...
Figure 1: Optimized geometry of transition structures TS1-A, TS1-B, and TS1-C computed at the B3LYP/6-31+G** ...