<MultiModal>![CC1=CC=C(C)C=C1.NC2=NC3=CC=CC=C3C=C2>[PIDA],[HFIP]>[A], A is the reaction product](/media/uploads/08ef091c-6ce1-46a3-8077-097692ff75c6.png)</MultiModal>

In the process of generating $\mathbf{A}$, $\mathrm{PIDA}$ first oxidizes p-xylene to a benzylic cation via a free radical mechanism. After being captured by aminoquinoline, it is further oxidized twice by PIDA to obtain product $\mathbf{A}$. Please try to deduce the structure of product $\mathbf{A}$ based on this hint. ($\mathrm{HFIP}$ is hexafluoroisopropanol)
<MultiModal>![CC1=CC=C(C)C=C1.NC2=NC3=CC=CC=C3C=C2>[PIDA],[HFIP]>[A],A为反应产物](/media/uploads/08ef091c-6ce1-46a3-8077-097692ff75c6.png)</MultiModal>

在生成 $\mathbf{A}$ 的历程中, $\mathrm{PIDA}$先通过自由基机理将对二甲苯氧化成苄基正离子，被氨基喹啉捕获后被PIDA继续氧化两次得到产物 $\mathbf{A}$。请根据此提示尝试推测出产物 $\mathbf{A}$ 的结构。（$\mathrm{HFIP}$为六氟异丙醇）
All other options are incorrect
<MultiModal>![CC1=CC2=C(N=C3N2C4=C(C=CC=C4)C=C3)C=C1](/media/uploads/78101ebb-91b1-4c30-8640-6a11ed1186eb.png)</MultiModal>
<MultiModal>![CC1=C2C(N(C(C=CC=C3)=C3C=C4)C4=N2)=C(C)C=C1](/media/uploads/faa81dca-4bd3-46ff-becd-421a8e09dcd1.png)</MultiModal>
<MultiModal>![CC1=CC2=C(N(C(C=CC=C3)=C3C=C4)C4=N2)C=C1](/media/uploads/e3d0c7d3-d6d9-4284-99bd-06ffb9b8cb66.png)</MultiModal>
<MultiModal>![CC1=CC2=C(C(N=C3N2C4=C(C=CC=C4)C=C3)=O)C=C1](/media/uploads/f0e00613-ac11-438c-a7bb-c696a07efc79.png)</MultiModal>
<MultiModal>![CC1=CC2=C(C(N(C(C=CC=C3)=C3C=C4)C4=N2)=O)C=C1](/media/uploads/1f607881-a1a4-4946-89e1-2d1e32a53866.png)</MultiModal>
其他选项均不正确
<MultiModal>![CC1=CC2=C(N=C3N2C4=C(C=CC=C4)C=C3)C=C1](/media/uploads/78101ebb-91b1-4c30-8640-6a11ed1186eb.png)</MultiModal>
<MultiModal>![CC1=C2C(N(C(C=CC=C3)=C3C=C4)C4=N2)=C(C)C=C1](/media/uploads/faa81dca-4bd3-46ff-becd-421a8e09dcd1.png)</MultiModal>
<MultiModal>![CC1=CC2=C(N(C(C=CC=C3)=C3C=C4)C4=N2)C=C1](/media/uploads/e3d0c7d3-d6d9-4284-99bd-06ffb9b8cb66.png)</MultiModal>
<MultiModal>![CC1=CC2=C(C(N=C3N2C4=C(C=CC=C4)C=C3)=O)C=C1](/media/uploads/f0e00613-ac11-438c-a7bb-c696a07efc79.png)</MultiModal>
<MultiModal>![CC1=CC2=C(C(N(C(C=CC=C3)=C3C=C4)C4=N2)=O)C=C1](/media/uploads/1f607881-a1a4-4946-89e1-2d1e32a53866.png)</MultiModal>
According to the question prompt, the benzylic cation intermediate generated in this reaction is first attacked by ammonia nucleophilically, and then the nitrogen atom combines with 1 molecule of oxidant $\mathrm{PIDA}$ to obtain the intermediate

<MultiModal>![CC1=CC=C(CN(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3)C=C1](/media/uploads/af7f10bb-a044-44e6-a93e-9819a94dfca2.png)</MultiModal>

<Checkpoint>[The first intermediate is CC1=CC=C(CN(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3)C=C1](1)</Checkpoint>

Then a phenyl migration reaction occurs to obtain the intermediate

<MultiModal>![C=[N+](C1=CC=C(C=CC=C2)C2=N1)C3=CC=C(C)C=C3](/media/uploads/b7c65d62-bbdb-4964-8a9a-9617336fc777.png)</MultiModal>

<Checkpoint>[Then a phenyl migration reaction occurs to obtain the intermediate: C=[N+](C1=CC=C(C=CC=C2)C2=N1)C3=CC=C(C)C=C3](1)</Checkpoint>

Subsequently, the intermediate is captured by the anion in the system

<MultiModal>![CC(C=C1)=CC=C1N(COC(C(F)(F)F)C(F)(F)F)C2=CC=C(C=CC=C3)C3=N2](/media/uploads/af768ec1-ddc9-454f-988e-199c9e7168e1.png)</MultiModal>

<Checkpoint>[The third intermediate: CC(C=C1)=CC=C1N(COC(C(F)(F)F)C(F)(F)F)C2=CC=C(C=CC=C3)C3=N2](1)</Checkpoint>

Then the secondary amine intermediate is reformed

<MultiModal>![CC(C=C1)=CC=C1NC2=CC=C(C=CC=C3)C3=N2](/media/uploads/9a281e2b-6213-4052-8d38-7421d329f8e7.png)</MultiModal>

<Checkpoint>[Secondary amine intermediate: CC(C=C1)=CC=C1NC2=CC=C(C=CC=C3)C3=N2](1)</Checkpoint>

Subsequently, the nitrogen atom combines again with 1 molecule of oxidant $\mathrm{PIDA}$

<MultiModal>![CC(C=C1)=CC=C1N(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3](/media/uploads/956a02ac-16ac-46e9-9091-ca08992a92df.png)</MultiModal>

<Checkpoint>[The fifth intermediate: CC(C=C1)=CC=C1N(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3](1)</Checkpoint>

The nitrogen atom performs nucleophilic attack on the benzene ring, yielding the intermediate

<MultiModal>![CC1=CC2[N+]3=C(N=C2C=C1)C=CC4=C3C=CC=C4](/media/uploads/97fe052d-854d-4f7a-9f3d-a38dfe13e449.png)</MultiModal>

<Checkpoint>[The sixth intermediate: CC1=CC2[N+]3=C(N=C2C=C1)C=CC4=C3C=CC=C4](1)</Checkpoint>

Finally, the final product is obtained via deprotonation and aromatization
根据题目提示，该反应生成的苄基正离子中间体首先被氨基亲核进攻，随后氮原子与1分子氧化剂$\mathrm{PIDA}$结合得到中间体

<MultiModal>![CC1=CC=C(CN(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3)C=C1](/media/uploads/af7f10bb-a044-44e6-a93e-9819a94dfca2.png)</MultiModal>

<Checkpoint>[第一个中间体是CC1=CC=C(CN(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3)C=C1](1)</Checkpoint>

接着发生苯基迁移反应得到中间体

<MultiModal>![C=[N+](C1=CC=C(C=CC=C2)C2=N1)C3=CC=C(C)C=C3](/media/uploads/b7c65d62-bbdb-4964-8a9a-9617336fc777.png)</MultiModal>

<Checkpoint>[接着发生苯基迁移反应得到中间体：C=[N+](C1=CC=C(C=CC=C2)C2=N1)C3=CC=C(C)C=C3](1)</Checkpoint>

随后该中间体被体系中的阴离子捕获

<MultiModal>![CC(C=C1)=CC=C1N(COC(C(F)(F)F)C(F)(F)F)C2=CC=C(C=CC=C3)C3=N2](/media/uploads/af768ec1-ddc9-454f-988e-199c9e7168e1.png)</MultiModal>

<Checkpoint>[第三个中间体：CC(C=C1)=CC=C1N(COC(C(F)(F)F)C(F)(F)F)C2=CC=C(C=CC=C3)C3=N2](1)</Checkpoint>

接着重新形成仲胺中间体

<MultiModal>![CC(C=C1)=CC=C1NC2=CC=C(C=CC=C3)C3=N2](/media/uploads/9a281e2b-6213-4052-8d38-7421d329f8e7.png)</MultiModal>

<Checkpoint>[仲胺中间体：CC(C=C1)=CC=C1NC2=CC=C(C=CC=C3)C3=N2](1)</Checkpoint>

随后氮原子再次结合1分子氧化剂$\mathrm{PIDA}$

<MultiModal>![CC(C=C1)=CC=C1N(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3](/media/uploads/956a02ac-16ac-46e9-9091-ca08992a92df.png)</MultiModal>

<Checkpoint>[第五个中间体：CC(C=C1)=CC=C1N(I(C2=CC=CC=C2)OC(C)=O)C3=CC=C(C=CC=C4)C4=N3](1)</Checkpoint>

氮原子对苯环进行亲核进攻，得到中间体

<MultiModal>![CC1=CC2[N+]3=C(N=C2C=C1)C=CC4=C3C=CC=C4](/media/uploads/97fe052d-854d-4f7a-9f3d-a38dfe13e449.png)</MultiModal>

<Checkpoint>[第六个中间体：CC1=CC2[N+]3=C(N=C2C=C1)C=CC4=C3C=CC=C4](1)</Checkpoint>

最后经去质子芳构化得到最终产物