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Please login to access the full content or check if you have access via31.9.2.1.4.7 Method 7: Arenesulfonamides via Reduction of Arenesulfonyl Azides
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Shcherbakova, I., Science of Synthesis, (2007) 31, 815.
Arenesulfonyl azides 140 are readily reduced by a number of reagents to arenesulfonamides 141 under mild conditions (Scheme 60).[168–179] In turn, arenesulfonyl azides can be conveniently prepared from arenesulfonyl halides and sodium azide (see Section 31.9.2.1.6.1). Thus, the reduction of arenesulfonyl azides is indirect transformation of the arenesulfonyl halides into arenesulfonamides in the absence of the nucleophilic and basic ammonia reagents (cf. Section 31.9.2.1.4.5.1). Such conditions are particularly important in the synthesis of arenesulfonamides with substituents that are sensitive to basic and/or nucleophilic reagents.
Meeeee 88 Meeeeeeeeeeeeeee eee Meeeeeeee ee Meeeeeeeeeeee Meeeee[888–888]
M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
M | Me | Me, MeMe8•8M8M, MMM, 8°M, 8 e | 88 | [888] |
M | Me | Me, MeMe8•8M8M, MMM, M8, 8°M, 88 eee | 88 | [888] |
M | Me | Me, MeMe8, MeMM, 8°M ee ee, 8.8 e | 88 | [888] |
M | M | Me, MeMe8•8M8M, MMM, M8, ee ee 88°M, 88 eee | 88 | [888] |
M | Me | Me, MeMe8•8M8M, MMM, M8, ee ee 88°M, 8.8 e | 88 | [888] |
M | M | Me, MeMM8, MMM, 8°M ee ee, 88 eee | 88 | [888] |
MM8M | MM | Me, MeMM8, MMM, 8°M ee ee, 88 eee | 88 | [888] |
M | Me | Me(MM8)8, MM8Me8, ee, 8.8 e | 88 | [888] |
M | MM8M | MeMM8, MeMe8•8M8M, M8M, ee, 88 eee | 88 | [888] |
M | MMMe | M88M88, Me/M, M8, ee, 88 eee | 88 | [888] |
M | Me | Me, M8, M8, MeMM, ee, 8 e, eeee eeeeee, 8 e | 88 | [888] |
M | Me | 88% ee MM, ee, 8.8 e | 88 | [888] |
M | M | Me8M•M8M, MeMM (8 eeeee), ee, 8 eee | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
8-Meeeeeeeeeeeeeeeeeeeeeeee (888, M8 = M; M8 = MM8M); Meeeeee Meeeeeeee:[888]
Me e eeeeeee ee eee 8-eeeeeeeeeeeeeee eeeee 888 (M8 = M; M8 = MM8M; 8,88 e, 8.8 eeee) eee MeMe8•8M8M (88 ee, 8.8 eeee) eee eeeee eeeeeeee e eeee ee MeMM8 (8.88 e, 8.8 eeee) ee M8M (8 eM), eeee eeeeeeee, ee ee. Mee eeeeeeeee ee e eeeee eeeeeeeeeee eeeeeeeee eee eeeeeeeee ee e eeeeee eeeeee eeeeeee. Mee eeeeeee eee eeeeeee eee 88 eee ee ee eee eeee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeee eeeeeee; eeeee: 8.88 e (88%).
Meeeeeeeeeeeeeeeee (888, M8 = M8 = M); Meeeeee Meeeeeeee:[888]
Meeeeeeeeeeeeee eeeee (8.8 e, 8.8 eeee) eee eeeeeeeee ee MMM (ee eMeMM, ee MeMM, ee MMMM) eeeeeeeeee Me (88 ee, 8.88 eeee). Mee eeeeeee eee eeeeee ee eee, eeee eeeeeeee, eee MeMM8 (8.8 e, 88 eeee) eee eeeee ee eeeee eeeeeeee; eeeeeeee eee eeeeeeeee ee ee eee 88 eee. Mee M8MM8 eee eeeee eee eee eeeeeee eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeeee eeee M8M eee eeeee (Me8MM8). Meeeeeeeeee ee eee eeeeeee ee ee eeeeeeee e eeee eeeee eeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
[168] | Meeeee, M.; Meeeee, M.; Meeeeeeee, M.; Meeeee, M. M., Meeeeee, (8888), 8888. |
[169] | Meeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meeeee, M. M., Meee. Meee., (8888), 888. |
[170] | Meeeee, M.; Meeeee, M. M.; Meeeeeeee, M.; Meeeee, M. M., Meee. Meee., (8888), 888. |
[171] | Me, M.; Meee, M.; Meeee, M., M. Meee. Mee., Meeee., (8888), 888. |
[172] | Me, M.; Meee, M.; Meeee, M., Meeee. Meeeee., (8888) 88, 888. |
[173] | Meeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 88, 88. |
[174] | Meee, M. M.; Meeeee, M.; Meeeeeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[175] | Meeeeeeeee, M.; Meeee, M.; Meeeeee, M., Meeeeeeee, (8888), 888. |
[176] | Meee, M. M.; Meeee, M. M.; Mee, M. M.; Meee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[177] | Meeee, M.; Meeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[178] | Meeee, M.; Meeee, M. M. M. M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[179] | Meeeee, M.; Meeeee, M. M.; Meeeeee, M., Meeeeeeeee, Meeeee Meeeeee Meeee. Meee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) M 88-8, 8888.