Q14 · CSIR NET Chemistry, December 2014
Paper: CSIR NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
The major product for the following reactions is 
$mathrm{I_2}$, $mathrm{PhI(OAc)_2}$ $mathrm{CH_2Cl_2}$, r.t.
$mathrm{I_2}$, $mathrm{PhI(OAc)_2}$ $mathrm{CH_2Cl_2}$, r.t.(a)
(b)
(c)
(d)
Answer
Answer: A ✓ checked by 4AB · confidence medium
Explanation
I₂/PhI(OAc)₂ forms the phosphoramidyl radical, which abstracts the δ C–H next to the ring oxygen (1,5-HAT); iodination and intramolecular displacement give the bridged N-phosphoryl aminal (a).
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