<MultiModal>![[H][C@@]1(CCCC2)[C@@]2([H])C/C1=N\OC(C3=CC=CC=C3)=O.C=C(C1=CC=CC=C1)C2=CC=CC=C2>$Cu(OTf)_2$  (10 mol%),$1,4-Dioxane/PhCF_3 (1:1)$>[A]](/media/uploads/0b8ef318-407e-47c0-9d41-226e93443ac2.png)</MultiModal>

Please select the most suitable product A and predict whether the Z/E configuration of the carbon-nitrogen double bond will affect the reaction selectivity.
<MultiModal>![[H][C@@]1(CCCC2)[C@@]2([H])C/C1=N\OC(C3=CC=CC=C3)=O.C=C(C1=CC=CC=C1)C2=CC=CC=C2>$Cu(OTf)_2$  (10 mol%),$1,4-Dioxane/PhCF_3 (1:1)$>[A]](/media/uploads/0b8ef318-407e-47c0-9d41-226e93443ac2.png)</MultiModal>

请选出最合适的产物 A，并预测碳氮双键的 Z/E 构型是否会对反应选择性产生影响
<MultiModal>![N#CC[C@@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/dc30a3d6-8bf6-4af7-babb-ac54d28639a0.png)</MultiModal>

No
<MultiModal>![N#CC[C@@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/5f389965-d5e4-4d15-ad2a-4356844d102f.png)</MultiModal>  

No
<MultiModal>![N#CC[C@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/1c76e4ab-6c26-4278-b012-6c919339b4b3.png)</MultiModal>

Yes
<MultiModal>![N#CC[C@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/64942cb7-754d-4691-8698-3cb10d071572.png)</MultiModal>  

Yes
<MultiModal>![N#CC[C@@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/dc30a3d6-8bf6-4af7-babb-ac54d28639a0.png)</MultiModal>  

Yes
<MultiModal>![N#CC[C@@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/5f389965-d5e4-4d15-ad2a-4356844d102f.png)</MultiModal>

Yes
<MultiModal>![N#CC[C@@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/dc30a3d6-8bf6-4af7-babb-ac54d28639a0.png)</MultiModal>

不会
<MultiModal>![N#CC[C@@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/5f389965-d5e4-4d15-ad2a-4356844d102f.png)</MultiModal>

不会
<MultiModal>![N#CC[C@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/1c76e4ab-6c26-4278-b012-6c919339b4b3.png)</MultiModal>

会
<MultiModal>![N#CC[C@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/64942cb7-754d-4691-8698-3cb10d071572.png)</MultiModal>

会
<MultiModal>![N#CC[C@@H]1[C@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/dc30a3d6-8bf6-4af7-babb-ac54d28639a0.png)</MultiModal>

会
<MultiModal>![N#CC[C@@H]1[C@@H](CCCC1)/C=C(C2=CC=CC=C2)/C3=CC=CC=C3](/media/uploads/5f389965-d5e4-4d15-ad2a-4356844d102f.png)</MultiModal>

会
This reaction is a free radical reaction

<Checkpoint>[This reaction is a free radical reaction](1)</Checkpoint>

$\mathrm{Cu}$ in the reaction system is a catalyst

<Checkpoint>[$\mathrm{Cu}$ in the reaction system is a catalyst](1)</Checkpoint>

$\mathrm{Cu(I)}$ first donates a single electron, causing the weaker \mathrm{N-O}$ bond to cleave, forming a free radical intermediate<MultiModal>![[H][C@@]1(CCCC2)[C@@]2([H])CC1=[N]](/media/uploads/a39bb79a-60bb-4adf-a361-4bfdcf160fbb.png)</MultiModal>

<Checkpoint>[$\mathrm{Cu(I)}$ first donates a single electron, causing the weaker N-O bond to cleave, forming a free radical intermediate](1)</Checkpoint>

The cleavage of the nitrogen-oxygen single bond is not the source of stereoselectivity, so the Z/E configuration of the carbon-nitrogen double bond will not affect the reaction selectivity.

<Checkpoint>[The cleavage of the nitrogen-oxygen single bond is not the source of stereoselectivity](1)</Checkpoint>

Subsequently, this unstable intermediate rapidly undergoes ring-opening, forming a more stable carbon radical<MultiModal>![[H][C]1[C@H](CC#N)CCCC1](/media/uploads/82ad13a0-bd77-4159-9717-c3ba617c7ecf.png)</MultiModal>

<Checkpoint>[Subsequently, this unstable intermediate rapidly undergoes ring-opening, forming a more stable carbon radical](1)</Checkpoint>

Then $\mathrm{Cu(II)}$ oxidizes this radical to form a carbocation<MultiModal>![N#CC[C@H]1[CH+]CCCC1](/media/uploads/b2d3b731-3852-470b-91a2-2d0c9f89bf0f.png)</MultiModal>

<Checkpoint>[Then $\mathrm{Cu(II)}$ oxidizes this radical to form a carbocation](1)</Checkpoint>

Since the steric hindrance above this carbocation is greater than that below, it is selectively captured by stilbene from below<MultiModal>![N#CC[C@H]1[C@@H](CCCC1)C[C+](C2=CC=CC=C2)C3=CC=CC=C3](/media/uploads/24cd58a1-07c6-4731-b330-3092f3c8ebcc.png)</MultiModal>

<Checkpoint>[Since the steric hindrance above this carbocation is greater than that below, it is selectively captured by stilbene from below](1)</Checkpoint>

Finally, deprotonation forms product A
该反应为自由基反应

<Checkpoint>[该反应为自由基反应](1)</Checkpoint>

反应体系中的 $\mathrm{Cu}$ 为催化剂

<Checkpoint>[反应体系中的 $\mathrm{Cu}$ 为催化剂](1)</Checkpoint>

$\mathrm{Cu(I)}$ 首先给出一个单电子，使得较弱的 \mathrm{N-O}$ 键发生裂解，形成自由基中间体<MultiModal>![[H][C@@]1(CCCC2)[C@@]2([H])CC1=[N]](/media/uploads/a39bb79a-60bb-4adf-a361-4bfdcf160fbb.png)</MultiModal>

<Checkpoint>[$\mathrm{Cu(I)}$ 首先给出一个单电子，使得较弱的 $\mathrm{N-O}$ 键发生裂解，形成自由基中间体](1)</Checkpoint>

其中氮氧单键的断裂并非立体选择性的来源，因此碳氮双键的 Z/E 构型不会对反应选择性产生影响

<Checkpoint>[氮氧单键的断裂并非立体选择性的来源](1)</Checkpoint>

随后该不稳定中间体迅速发生开环，形成较稳定的碳自由基<MultiModal>![[H][C]1[C@H](CC#N)CCCC1](/media/uploads/82ad13a0-bd77-4159-9717-c3ba617c7ecf.png)</MultiModal>

<Checkpoint>[随后该不稳定中间体迅速发生开环，形成较稳定的碳自由基](1)</Checkpoint>

接着 $\mathrm{Cu(II)}$ 将该自由基氧化，形成碳正离子<MultiModal>![N#CC[C@H]1[CH+]CCCC1](/media/uploads/b2d3b731-3852-470b-91a2-2d0c9f89bf0f.png)</MultiModal>

<Checkpoint>[接着 $\mathrm{Cu(II)}$ 将该自由基氧化，形成碳正离子](1)</Checkpoint>

由于该碳正离子上方的位阻大于下方，因此被二苯乙烯选择性地从下方捕获<MultiModal>![N#CC[C@H]1[C@@H](CCCC1)C[C+](C2=CC=CC=C2)C3=CC=CC=C3](/media/uploads/24cd58a1-07c6-4731-b330-3092f3c8ebcc.png)</MultiModal>

<Checkpoint>[由于该碳正离子上方的位阻大于下方，因此被二苯乙烯选择性地从下方捕获](1)</Checkpoint>

最后脱去质子形成产物 A