Q58 · CSIR NET Chemistry, June 2014
Paper: CSIR NET June 2014 · Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Sigmatropic Shifts · Marks: 2 · Difficulty: Hard
Pericyclic reaction involved in one of the steps of the following reaction sequence is 
(i) heat 
(ii) $\mathrm{(EtO)_3P}$ 
(i) heat (ii) $\mathrm{(EtO)_3P}$ (a)[1, 3] sigmatropic shift
(b)[3, 3] sigmatropic shift
(c)[1, 5] sigmatropic shift
(d)[2, 3] sigmatropic shift
Answer
Answer: D ✓ checked by 4AB · confidence high
Explanation
Heating an allyl phenyl sulfoxide gives a [2,3]-sigmatropic (Mislow–Evans) rearrangement to the allyl sulfenate, which (EtO)₃P cleaves to the allylic alcohol.
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