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Unraveling the mechanism of cascade reactions of zincke aldehydes.

Abstract:

The thermal pericyclic cascade rearrangement of Zincke aldehydes (5-(dialkylamino)-2,4-pentadienals) to afford Z-α,β,γ,δ-unsaturated amides discovered by the Vanderwal group has been studied in depth using quantum mechanical methods. Two mechanistic possibilities that had previously been put forth to explain this internal redox process, one that had been discounted by experiment and the other that had withstood experimental scrutiny, were evaluated. Both of these mechanisms suffered from ener...

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Publication status:
Published

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Publisher copy:
10.1021/ja107988b

Authors


Journal:
Journal of the American Chemical Society
Volume:
133
Issue:
11
Pages:
3895-3905
Publication date:
2011-03-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:ef4e745f-14d5-43bb-9778-ffc7660ae246
Source identifiers:
135022
Local pid:
pubs:135022

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