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1 article(s) from Marin-Luna, Marta

Tandem processes promoted by a hydrogen shift in 6-arylfulvenes bearing acetalic units at ortho position: a combined experimental and computational study

Mateo Alajarin,
Marta Marin-Luna,
Pilar Sanchez-Andrada and
Angel Vidal

Beilstein J. Org. Chem. 2016, 12, 260–270, doi:10.3762/bjoc.12.28

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Scheme 1: Lewis acid-catalyzed [1,4]-H transfer/1,5-electrocyclization tandem processes of benzylidenemalonat...

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Scheme 2: Preparation of benz[f]indenes 5 and 6. Reagents and conditions: i) cyclopentadiene, pyrrolidine, an...

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Scheme 3: Postulated reaction path for the conversion 3a → 5a + 6a initiated by a [1,4]-hydride shift.

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Scheme 4: Alternative mechanistic paths for the conversion 3a → 5a + 6a initiated by [1,5]-, [1,7]- or [1,9]-...

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Scheme 5: Postulated outcome of the conversion 14 → 18 + 19 initiated by a [1,4]-deuteride shift.

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Scheme 6: Preparation of deuterated benz[f]indenes 18 + 19 and 21 + 22. Reagents and conditions: i) DMSO, mic...

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Scheme 7: Reagents and conditions: i) triethylamine (10%), DMSO, rt, 2 h.

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Scheme 8: Preparation of benz[f]indenes 25 and 26. Reagents and conditions: i) cyclopentadiene, pyrrolidine, ...

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Scheme 9: Mechanistic paths for the conversion of fulvene 3a into the benz[f]indenes 5a and 6a showing the en...

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Figure 1: Optimized geometry of transition structures TS1-A, TS1-B, and TS1-C computed at the B3LYP/6-31+G** ...

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Published 11 Feb 2016

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