The Arndt-Eistert synthesis involves a rearrangement (known as a Wolff Rearrangement) with concomitant evolution of nitrogen gas. This reaction has been modified by Georg (J. Am. Chem. Soc. 2010, 132, 15512) to result in a "vinylogous" Wolff Rearrangement (not covered in class). Propose a mechanism for Georg's variation shown below (hint: there's a ketene intermediate). BNCODE Bn- OEt N₂

Organic Chemistry: A Guided Inquiry
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Author:Andrei Straumanis
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Chapter21: Nas: Nucleophilic Aromatic Substitution
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The Arndt-Eistert synthesis involves a rearrangement (known as a Wolff Rearrangement) with
concomitant evolution of nitrogen gas. This reaction has been modified by Georg (J. Am. Chem. Soc.
2010, 132, 15512) to result in a "vinylogous" Wolff Rearrangement (not covered in class). Propose a
mechanism for Georg's variation shown below (hint: there's a ketene intermediate).
Bn.
N
O
OEt
№₂
Bn
CO₂Et
Transcribed Image Text:The Arndt-Eistert synthesis involves a rearrangement (known as a Wolff Rearrangement) with concomitant evolution of nitrogen gas. This reaction has been modified by Georg (J. Am. Chem. Soc. 2010, 132, 15512) to result in a "vinylogous" Wolff Rearrangement (not covered in class). Propose a mechanism for Georg's variation shown below (hint: there's a ketene intermediate). Bn. N O OEt №₂ Bn CO₂Et
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