※ 引述《life2002 (あいたい)》之銘言：
: 最近我們教到醚類
: 講到claisen rearrangement時
: 老師出了一個問題
: 若 3-benzoxy-1-butene做claisen rearrangment時
: 其產物以及反應機構會是什麼??
: 老師說這跟[3,3]sigmatropic rearrangement有關
: 但是我們還沒教到這邊
: 偏偏老師又說這是考試題目阿阿阿~~~~
: 所以請高手替我解答一下 感激萬分.....
Claisen rearrangement follows [3,3]-sigmatropic rearrangement mechanism.
Thus the product is 2-(but-2-enyl)phenol, both E and Z isomer in 1:1 ratio.
This [3,3]-sigmatropic rearrangement could occur when the starting
material contains following skeleton:
C=C-X-C-C=C, X=C, O, N...
As the conformation of compd. containing above skeleton is twisted
to the chair form, A new C-C bond generates between C1 and C6, and
the bond between X3 and C4 breaks. New double bonds forms between
C2, X3 and C4, C5. All the bond formation and breaking are simul-
taneously.
The starting material you gave will be converted into a new compd.
"6-(but-2-enyl)cyclohexa-2,4-dienone", and followed by rearomatization
to generate the final product I told.
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