<MultiModal>![O=C(CNC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2.C[Si](C)(C#N)C>[DBU],[DMF]>[A], A is the reaction product, the reaction is carried out in air.](/media/uploads/bd68357b-c6a3-4b58-a90a-f49d712b07fd.png)</MultiModal>

Given that the reaction involves a free radical transformation process. Please try to predict the structural formula of the main product $\mathbf{A}$ and the side product $\mathbf{B}$ (molecular formula: $\mathrm{C_{17}H_{14}ClNO_2}$) without a cyano group.
<MultiModal>![O=C(CNC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2.C[Si](C)(C#N)C>[DBU],[DMF]>[A],A为反应产物,反应在空气中进行](/media/uploads/bd68357b-c6a3-4b58-a90a-f49d712b07fd.png)</MultiModal>

已知该反应包含自由基转化过程。请尝试预测该反应的主产物$\mathbf{A}$以及不含氰基的副产物$\mathbf{B}$（分子式：$\mathrm{C_{17}H_{14}ClNO_2}$）的结构式
All other options are incorrect.
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, Main product $\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2, Byproduct $\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

Byproduct $\mathbf{B}$
<MultiModal>![O=C(C(C#N)NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, Main product $\mathbf{A}$](/media/uploads/c9bf7be9-9d1d-4296-98bd-d227828918c9.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2, Byproduct $\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

Byproduct $\mathbf{B}$
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, Main product $\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3, Byproduct $\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

Byproduct $\mathbf{B}$
<MultiModal>![O=C(C(C#N)N(O1)C2=CC=C(C)C=C2)C=C1C3=CC=C(Cl)C=C3, Main product $\mathbf{A}$](/media/uploads/990e77cf-b2d8-4551-aea0-a5fd5ff54df0.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3, Byproduct $\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

Byproduct $\mathbf{B}$
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, main product $\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(/C=[N+]([O-])/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, byproduct $\mathbf{B}$](/media/uploads/8a1ac710-11cb-4e79-8d07-dc00fe86ad02.png)</MultiModal>

Byproduct $\mathbf{B}$
<MultiModal>![O=C(C(C#N)NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2, Main product $\mathbf{A}$](/media/uploads/c9bf7be9-9d1d-4296-98bd-d227828918c9.png)</MultiModal>

Main product $\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3, Byproduct $\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

Byproduct $\mathbf{B}$
其他选项均不正确
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

副产物$\mathbf{B}$

<MultiModal>![O=C(C(C#N)NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/c9bf7be9-9d1d-4296-98bd-d227828918c9.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

副产物$\mathbf{B}$
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3,副产物$\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

副产物$\mathbf{B}$
<MultiModal>![O=C(C(C#N)N(O1)C2=CC=C(C)C=C2)C=C1C3=CC=C(Cl)C=C3,主产物$\mathbf{A}$](/media/uploads/990e77cf-b2d8-4551-aea0-a5fd5ff54df0.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3,副产物$\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

副产物$\mathbf{B}$
<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(/C=[N+]([O-])/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$](/media/uploads/8a1ac710-11cb-4e79-8d07-dc00fe86ad02.png)</MultiModal>

副产物$\mathbf{B}$
<MultiModal>![O=C(C(C#N)NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/c9bf7be9-9d1d-4296-98bd-d227828918c9.png)</MultiModal>

主产物$\mathbf{A}$

<MultiModal>![O=C(C(N(O1)C2=CC=C(C)C=C2)=O)C=C1C3=CC=C(Cl)C=C3,副产物$\mathbf{B}$](/media/uploads/6ddb5336-7847-4634-8074-1c089d62f399.png)</MultiModal>

副产物$\mathbf{B}$

According to the chemical formula of the byproduct, oxidation occurred during the formation of the byproduct; the number of carbon atoms remained unchanged, but one more oxygen atom was added. Combined with the reaction conditions, it can be concluded that the oxygen donor can only be oxygen from the air, and oxygen can be used as a free radical initiator to initiate the free radical transformation process mentioned in the question.

<Checkpoint>[Oxygen as a free radical initiator](1)</Checkpoint>

First, the substrate is deprotonated under the action of the base $\mathrm{DBU}$ to form intermediate 1.

<MultiModal>![[O-]C(/C=C/C1=CC=C(Cl)C=C1)=C\NC2=CC=C(C)C=C2](/media/uploads/8bc2176f-ee19-46c5-98da-1dc000fa1368.png)</MultiModal>

<Checkpoint>[[O-]C(/C=C/C1=CC=C(Cl)C=C1)=C\NC2=CC=C(C)C=C2](1)</Checkpoint>

Then, it is deprived of an electron by oxygen to form a superoxide anion radical and a free radical intermediate 2.

<MultiModal>![O=C(C([X])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X is a single electron](/media/uploads/102a30e4-916b-4000-b057-e0578903417d.png)</MultiModal>

<Checkpoint>[O=C(C([X])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X is a single electron](1)</Checkpoint>

The free radical combines with the superoxide anion radical to obtain intermediate 3.

<MultiModal>![O=C(C(O[O-])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/63f2a0ab-ca16-47a2-a3b7-07e6237bbaad.png)</MultiModal>

<Checkpoint>[O=C(C(O[O-])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

Subsequently, an elimination reaction occurs to obtain intermediate 4.

<MultiModal>![O=C(/C=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/dd8d9223-aabc-454f-8665-60fdaff6a1ae.png)</MultiModal>

<Checkpoint>[O=C(/C=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

If only one molecule of $\mathrm{H_2O}$ is eliminated here, byproduct $\mathbf{B}$ will be obtained, which also matches the chemical formula given in the question.

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

<Checkpoint>[O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$](1)</Checkpoint>

Intermediate 4 undergoes a rapid addition reaction with $\mathrm{TMSCN}$ to obtain intermediate 5.

<MultiModal>![O=C(C(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/ad9759e6-a426-4308-879f-196c8d9da45e.png)</MultiModal>

<Checkpoint>[O=C(C(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

This intermediate 5 is further deprived of 1 electron by oxygen to form a free radical intermediate 6.

<MultiModal>![O=C(C([X])(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X为单电子](/media/uploads/c1744f9f-90a4-44bf-92bf-80e0e5040756.png)</MultiModal>

<Checkpoint>[O=C(C([X])(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X为单电子](1)</Checkpoint>

This free radical intermediate combines with the superoxide anion radical to obtain intermediate 7.

<MultiModal>![O=C(C(N([Si](C)(C)C)C1=CC=C(C)C=C1)(O[O-])C#N)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/cd656465-6284-4e06-b050-2b491cd2b917.png)</MultiModal>

<Checkpoint>[O=C(C(N([Si](C)(C)C)C1=CC=C(C)C=C1)(O[O-])C#N)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

Finally, a molecule of $\mathrm{TMS}$-superoxide anion is removed to obtain the main product $\mathbf{A}$.

<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

<Checkpoint>[O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](1)</Checkpoint>
根据副产物的化学式可知生成副产物的过程中发生了氧化，碳数不变而多了一个氧，结合反应条件可知氧供体只能是来自空气的氧气，而氧气便可作为自由基引发剂引发题干所说的自由基转化过程。

<Checkpoint>[氧气作为自由基引发剂](1)</Checkpoint>

首先底物在碱$\mathrm{DBU}$的作用下去质子形成中间体1

<MultiModal>![[O-]C(/C=C/C1=CC=C(Cl)C=C1)=C\NC2=CC=C(C)C=C2](/media/uploads/8bc2176f-ee19-46c5-98da-1dc000fa1368.png)</MultiModal>

<Checkpoint>[[O-]C(/C=C/C1=CC=C(Cl)C=C1)=C\NC2=CC=C(C)C=C2](1)</Checkpoint>

随后被氧气夺取一个电子形成超氧阴离子自由基和自由基中间体2

<MultiModal>![O=C(C([X])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X是单电子](/media/uploads/102a30e4-916b-4000-b057-e0578903417d.png)</MultiModal>

<Checkpoint>[O=C(C([X])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X是单电子](1)</Checkpoint>

该自由基与超氧阴离子自由基结合得到中间体3

<MultiModal>![O=C(C(O[O-])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/63f2a0ab-ca16-47a2-a3b7-07e6237bbaad.png)</MultiModal>

<Checkpoint>[O=C(C(O[O-])NC1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

随后发生消除反应得到中间体4

<MultiModal>![O=C(/C=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/dd8d9223-aabc-454f-8665-60fdaff6a1ae.png)</MultiModal>

<Checkpoint>[O=C(/C=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

此处如果只消除1分子$\mathrm{H_2O}$的话，将得到副产物$\mathbf{B}$，这也符合题目给出的化学式。

<MultiModal>![O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}$
](/media/uploads/b4fd8f48-e8c0-4b7c-bb49-39f0f7a5bc78.png)</MultiModal>

<Checkpoint>[O=C(C(NC1=CC=C(C)C=C1)=O)/C=C/C2=CC=C(Cl)C=C2,副产物$\mathbf{B}](1)</Checkpoint>

中间体4与$\mathrm{TMSCN}$发生快速的加成反应得到中间体5

<MultiModal>![O=C(C(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/ad9759e6-a426-4308-879f-196c8d9da45e.png)</MultiModal>

<Checkpoint>[O=C(C(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

该中间体5进一步被氧气夺去1个电子形成自由基中间体6

<MultiModal>![O=C(C([X])(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X为单电子](/media/uploads/c1744f9f-90a4-44bf-92bf-80e0e5040756.png)</MultiModal>

<Checkpoint>[O=C(C([X])(C#N)N([Si](C)(C)C)C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,X为单电子](1)</Checkpoint>

该自由基中间体与超氧阴离子自由基结合得到中间体7

<MultiModal>![O=C(C(N([Si](C)(C)C)C1=CC=C(C)C=C1)(O[O-])C#N)/C=C/C2=CC=C(Cl)C=C2](/media/uploads/cd656465-6284-4e06-b050-2b491cd2b917.png)</MultiModal>

<Checkpoint>[O=C(C(N([Si](C)(C)C)C1=CC=C(C)C=C1)(O[O-])C#N)/C=C/C2=CC=C(Cl)C=C2](1)</Checkpoint>

最后脱去一分子$\mathrm{TMS}$-超氧阴离子得到主产物$\mathbf{A}$

<MultiModal>![O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](/media/uploads/e22567e6-04f6-460e-b4fa-586e213e36cd.png)</MultiModal>

<Checkpoint>[O=C(/C(C#N)=N/C1=CC=C(C)C=C1)/C=C/C2=CC=C(Cl)C=C2,主产物$\mathbf{A}$](1)</Checkpoint>