Does rearrangement undertook in wittig reactions

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter10: Oxidation And Reduction
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Does rearrangement undertook in wittig reactions
 
 
H₂
Ph
+
Ph
-Ph
The Mechanism of the Wittig Reaction
new C-C bond
H₂C-PPh3
oxaphosphetane
Step 1. Nucleophilic addtion to
C=O forming two bonds and in a
four-membered ring.
=CH₂ + (Ph)3P=O
Alkene
Step 2. Fragmentation of oxaphosphetane
by elimination of Ph3P=O and the desired
product alkene.
Transcribed Image Text:H₂ Ph + Ph -Ph The Mechanism of the Wittig Reaction new C-C bond H₂C-PPh3 oxaphosphetane Step 1. Nucleophilic addtion to C=O forming two bonds and in a four-membered ring. =CH₂ + (Ph)3P=O Alkene Step 2. Fragmentation of oxaphosphetane by elimination of Ph3P=O and the desired product alkene.
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