22.16 Nitrosation of Alkylamines
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1 22.16 itrosation of Alkylamines
2 itrite Ion, itrous Acid, and itrosyl Cation O O O O O O O O
3 itrosyl Cation and itrosation O
4 itrosyl Cation and itrosation O O
5 itrosation of Secondary Alkylamines O O O nitrosation of secondary amines gives an -nitroso amine
6 Example (C 3 ) 2 ao 2, Cl 2 O (C 3 ) 2 (88-90%) O
7 Some -itroso itroso Amines (C 3 ) 2 O -nitrosodimethylamine (leather tanning) O -nitrosopyrrolidine (nitrite-cured bacon) O -nitrosonornicotine (tobacco smoke)
8 itrosation of Primary Alkylamines R O R O R O analogous to nitrosation of secondary amines to this point
9 itrosation of Primary Alkylamines R O this species reacts further
10 itrosation of Primary Alkylamines R O R O
11 itrosation of Primary Alkylamines R O R O
12 itrosation of Primary Alkylamines R O R O
13 itrosation of Primary Alkylamines R O
14 itrosation of Primary Alkylamines nitrosation of a primary alkylamine gives an alkyl diazonium ion process is called diazotization R R O O
15 Alkyl Diazonium Ions R R alkyl diazonium ions readily lose 2 to give carbocations
16 Example: itrosation of 1,1-Dimethylpropylamine 2 OO O 2 O 2 (80%) Fig (p 890) (3%) (2%)
17 itrosation of Tertiary Alkylamines There is no useful chemistry associated with the nitrosation of tertiary alkylamines. R R R R O R R
18 22.17 itrosation of ylamines
19 itrosation of Tertiary ylamines reaction that occurs is electrophilic aromatic substitution (C 2 C 3 ) 2 1. ao 2, Cl, 2 O, 8 C 2. O (C 2 C 3 ) 2 (95%) O
20 itrosation of -Alkylarylamines similar to secondary alkylamines; gives -nitroso amines C 3 ao 2, Cl, 2 O, 10 C O C 3 (87-93%)
21 itrosation of Primary ylamines gives aryl diazonium ions aryl diazonium ions are much more stable than alkyl diazonium ions most aryl diazonium ions are stable under the conditions of their formation (0-10 C)
22 itrosation of Primary ylamines gives aryl diazonium ions aryl diazonium ions are much more stable than alkyl diazonium ions most aryl diazonium ions are stable under the conditions of their formation (0-10 C) fast R R 2 slow 2
23 Example: (C 3 ) 2 C 2 ao 2, 2 SO 4 2 O, 0-5 C0 (C 3 ) 2 C SO 4
24 Synthetic Origin of yl Diazonium Salts O 2 2
25 22.18 Synthetic Transformations of yl Diazonium Salts
26 Transformations of yl Diazonium Salts Cl Br C F I O
27 Preparation of Phenols hydrolysis of a diazonium salt 2 O, heat O
28 Example (C 3 ) 2 C 2 1. ao 2, 2 SO 4 2 O, 0-5 C O, heat (C 3 ) 2 C O (73%)
29 Transformations of yl Diazonium Salts Cl Br C F I O
30 Preparation of yl Iodides reaction of an aryl diazonium salt with potassium iodide KI I
31 Example 2 Br 1. ao 2, Cl 2 O, 0-5 C0 I Br 2. KI, room temp. (72-83%)
32 Transformations of yl Diazonium Salts Cl Br C F I O
33 Preparation of yl Fluorides F heat the tetrafluoroborate salt of a diazonium ion; process is called the Schiemann reaction
34 Example 2 1. ao 2, Cl, 2 O, 0-5 C0 F CC 2 C 3 O 2. BF 4 3. heat (68%) CC 2 C 3 O
35 Transformations of yl Diazonium Salts Cl Br C F I O
36 Preparation of yl Chlorides and Bromides Cl Br aryl chlorides and aryl bromides are prepared by heating a diazonium salt with copper(i) chloride or bromide substitutions of diazonium salts that use copper(i) halides are called Sandmeyer reactions
37 Example 2 1. ao 2, Cl, 2 O, 0-5 C0 Cl O 2 2. CuCl, heat O 2 (68-71%)
38 Example 2 Cl 1. ao 2, Br, 2 O, 0-10 C0 Br Cl 2. CuBr, heat (89-95%) 95%)
39 Transformations of yl Diazonium Salts Cl Br C F I O
40 Preparation of yl itriles C aryl nitriles are prepared by heating a diazonium salt with copper(i) cyanide this is another type of Sandmeyer reaction
41 Example 2 C 3 1. ao 2, Cl, 2 O, 0 C C C 3 2. CuC, heat (64-70%)
42 Transformations of yl Diazonium Salts Cl Br C F I O
43 Transformations of yl Diazonium Salts hypophosphorous acid ( 3 PO 2 ) reduces diazonium salts; ethanol does the same thing this is called reductive deamination
44 Example 2 C 3 ao 2, 2 SO 4, 3 PO 2 C 3 (70-75%) 75%)
45 Value of Diazonium Salts 1) allows introduction of substituents such as O, F, I, and C on the ring 2) allows preparation of otherwise difficultly accessible substitution patterns
46 Example 2 Br 2 Br 2 Br ao 2, 2 SO 4, 2 O, C 3 C 2 O 2 O Br (100%) Br Br Br (74-77%) 77%)
47 22.19 Azo Coupling
48 Azo Coupling Diazonium salts are weak electrophiles. React with strongly activated aromatic compounds by electrophilic aromatic substitution.
49 Azo Coupling Diazonium salts are weak electrophiles. React with strongly activated aromatic compounds by electrophilic aromatic substitution. ' ' an azo compound ' must bear a strongly electron-releasing releasing group such as O, OR, or R 2.
50 Example O C 6 5 Cl O C 6 5
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