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Schaumann, E., Science of Synthesis, (2009) 40, 1.
General Introduction
This volume of Science of Synthesis covers the syntheses of compounds having a single bond between an sp3-hybridized carbon atom and a formally sp3-hybridized nitrogen substituent. As an aid to organization it has been split into two parts which are, respectively, Science of Synthesis, Volume 40a (Amines and Ammonium Salts) and Science of Synthesis, Volume 40b (Amine N-Oxides, Haloamines, Hydroxylamines and Sulfur Analogues, and Hydrazines). Among the product classes featured, one of the most prominent representatives is the aliphatic amines (Section 40.1); however, separate sections are devoted to propargylic (Section 40.1.2) and allylic amines (Section 40.1.3) for which special synthetic methods are available, or where special care must be taken to secure synthetic success. Similarly, compounds with more than one amino group or an additional phosphorus functionality are treated separately (Section 40.1.4), as are the obviously special small-ring amine derivatives aziridines (Section 40.1.5) and azetidines (Section 40.1.6). Furthermore, the amino group may be modified in the form of ammonium compounds or of N-ylides (“ammonioalkanides”; Section 40.1.7). There is also a wide range of functionalities where a parent amine structure is combined with one heteroatom. This type of compound is seen in nitroxyl radicals (nitroxides; Section 40.2), amine N-oxides (Section 40.3), N-haloamines (Section 40.4), hydroxylamines (“N-hydroxyamines”) in acyclic (Section 40.5) or in cyclic form (Section 40.6), and hydrazines, again in acyclic (Section 40.7) or in cyclic form (Section 40.8), as well as extended hydrazines (Section 40.9). Finally, amido derivatives of sulfur-derived acids, specifically of sulfanediol (Section 40.10), of sulfurous acid (Section 40.11), and of sulfuric acid (Section 40.12) are covered. Ammonium sulfonates, thiohydroxylamines, and aminosulfonium salts are also featured (Section 40.13). For a ready overview, these structures are compiled in Table 1.
Meeee 8 Meeeeee ee Meeeee eee Meeee Meeeeeeeeee Meeeeee ee Meeeee 88
| Meeeeee Meeee ee Meeeeeee | Meeeeeeee(e) | Meeeeee |
|---|---|---|
| eeeee eeeeeeeee | 88.8 | |
| eeeee eee eeeeeeeeeeeeeeee |  |
88.8.8 |
| eeeeeeeeeee eeeeee | |
88.8.8 |
| eeeeeee eeeeee | |
88.8.8 |
| e-eeeeeeee- ee e-eeeeeeeeee-eeeeeeeeeeeeee eeeeeeeeeee (e ≥8) | |
88.8.8 |
| eeeeeeeeee | |
88.8.8 |
| eeeeeeeeee | |
88.8.8 |
| eeeeeeee eeeeeeeee | |
88.8.8.8.8–88.8.8.8.8 |
| eeeeeeee eeeeee | |
88.8.8.8.8 |
| eeeeeeee eeeeeeee (eeeeeeeeee) | |
88.8 |
| eeeee M-eeeeee | |
88.8 |
| M-eeeeeeeeee | |
88.8 |
| eeeeeeeeeeeeee | |
88.8 |
| 8-eee-8-eeeeeeeeeeeeeee | |
88.8 |
| eeeeeeeeee eee eeeeeeeeeee eeeee | |
88.8 |
| 8,8-eeeeeeeeeeeeeeeee | |
88.8 |
| eeeeeeeee eee eeeeeeeeee | |
88.8 |
| eeeee eeeeeeeeeee ee eeeeeeeeeee | |
88.88 |
| eeeee eeeeeeeeeee ee eeeeeeeee eeee | |
88.88.8–88.88.8 |
| M-(eeee)eeeeeeeeeeeeee | |
88.88.8, 88.88.8 |
| M,M′-eeeeeeeeeeeee eeeeeeee | |
88.88.8 |
| M-eeeeeeeeeeeee eeeee eee eeeeeeeeeee | |
88.88 |
| eeeeeeeeeeeeeeeeee, eeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeeee eeeee | |
88.88 |
Mee e eeeeeee eeeee ee ee eeeeeeee ee Meeeee 88, eee eeeeeeeee ee Meeeeee ee Meeeeeeee eeeeeeee eeee eee eeeeee ee eee M—M eeee ee ee8 eeeeeeeeee. Mee eeeeeeeee ee eeeeeeee 8 (M = MM8) ee eeeeeee ee Meeeeee ee Meeeeeeee, Mee. 88 [Meeee Meeeee—Meeeeeeeee Meeee: Meeeee Meeeeee eee Mee—M Meeeeeeee (Meeeeee 88.8.8.8)] eee eee eeeeeeeee ee eeeeeeeeee 8 (M = M), eeeee ee ee-eeeeeeeeee eeeeee ee eeeeee ee eee eeeeeeee, ee eeeeeeeee ee Mee. 88 [Meee Meeeee—Meeeeeeeee Meeee: M—M≡M, M=M=M, M8M=M, MM8 (Meeeeee 88.8.8)]. Me eee eeeeee ee ee8 eeeeeeeeee, ee ee eeeeeee eeeeeeeee 8, eee eeeeeeee eee ee eeeeeeee 8 (M = MM8M8) {eee Meeeeee ee Meeeeeeee, Mee. 88 [Mee—M Meeeeeeee (M = M, Me, Me, M, M) (Meeeeee 88.8.888.8.8)]} ee eeeee-eeee eeeeeeeeeee 8 (M = M ee eeeeeeeeeeeeeee), eeeeeee ee eeeeeeee eeee eeeeeeeeeee ee Meeeeee ee Meeeeeeee, Mee. 88 (Meee Meeeee—Meeeeeeeee Meeee: M—M≡M, M=M=M, M8M=M, MM8), eee ee eeeeeeeeee eeee eeeeee ee Mee. 88 (Meeee Meeeee—Meeeeeeeee Meeee: Meeeee eee Meeeeeeeeee; Meeeeeee; Meeeeee), eee ee eeeee eeeeeeeeeeeeeee ee Mee. 88 (Meeee Meeeee—Meeeeeeeee Meeee: Meee-, Meeeee-, eee Meeeeeeeeeeeeeeee Meeee eee Meeeeeeeeee; Meeeee Meeee eee Meeeeeeeeee; Meeee Meee Meeeeeeeeee). Meeeeeeee 8 eeee ee MM8 eeee ee e eeeeee ee e eeeeeeeeeeeeee eeee (e ≥8) eee eee eeeeeee ee Meeeeeee 8 (Meeeeeeee eee Meeeeee Meee Meeeeee; Meee. 8–88).
Meeeeeeee eeeeeeee eeeeeeeee 8 eeee e eeeeee eeee ee eeeeeee eeeeeeeeee eee eee eeeeeee ee Meeeeee ee Meeeeeeee, Mee. 88 (Meeee, Meeeeee, Mee, Meeee, eee Meeeeeeee Meeeeeeee, Meeeee, Meeeeeeee, eee Meeeeeeeee) ee eee eeeeeeee eeeeeeeeeeeeeee eeee eee eeeee eeeeeeeeeee ee eee eeeeeeee ee ee 8 eee 8. Meeeeeeee 8 (“eeeeeee eeeeeee”) eeeeeeee eeeeeeeee eeeeeeeeeee 8 (M = M = MM88). Meeeeee, eeee eeeeeee eeeee ee eeee, eeeeeeeee 8 eee eeeeeeee eeeeeeeeee (“eeeeeeeee” eeee e = 8, “eeeeeeeeee” eeee e = 8) eee eeeeeeeee eee eeeeeeeee eeee ee Meeeeee 88.8
Meeee ee eee eeeeeeee eeeee ee Meeeeee ee Meeeeeeee, ee8 eeeeeeeeeeeee ee eee eeeeee ee eee M—M eeee ee eee e eeeeeeeeee eeeeeeeee eee eeeeeeeee ee eee eeeeeee eeeeee; ee eeeeeeee, ee eeeee eeeeeeeeee ee eee eeeeeeeeeee eeeeee ee eeeeeee. Meeeeeeee, ee eeeeeee eeeeeeeeee eeeee ee eeeeee eeeeeeee ee eeeeeee ee eee eeeeeeeeeee eeeeee, eee eeeeeeeee ee eeeeeee ee eee eeeeeeee ee eeee eeeee. Meeeeee, eeeeeeeee eeee eeeeeeee—eeeee eeeee eee eeeeeee ee Meeeeeee 8 (Meeeeeeeeeeeeee; Meee. 8–8). Me eeeeeeee ee eee eeeeeeee ee eee eeeeeeeee eeeee ee eeeeee eeeee eeeeeeeeeee ee eeeee ee Meeee 8. Me eee eeee, ee eee eee eeee eeeeeeeeeee eeee ee eeeeeeeee ee Meeeeee ee Meeeeeeee ee eeeee eeeeeeeeeee, e eeeeeeeeeeee eeeeee ee eee eeeeeeeeee eeeeeee ee eeeeeeeeeee.
Meeee 8 Meeee Meeee Meeeeeeeee Meeeeeeeee Meeee Meeeeee Meeeeeeee ee Meeeeee ee Meeeeeeee
| Meee | Meeeeeeee(e) | Meeeee | Meeeeee |
|---|---|---|---|
| eeeeeeeeeeee, eeeeee–eeeee eeeeeeeee | |
8 (Meeee Meeeeeeee) | 8.8.88 |
| M-(eeeeeeeeeeee)eeeeee | |
8.8.88.8 | |
| eeeee–eeeeeeeee eeeeeeeee | MeMeM8-e(MM8M8)e, MeMeM8•MM8M8M8 | 8 [Meeeeeeee ee Meeeee 88 eee 8 (Me, Me, Me, Me, Me…Me)] | 8.8.8.88 |
| eeeeeeeeeeeeee eeeeee | |
8.8.8 | |
| eeeeeeeee eeeeee | (M8M8M)8Me | 8.8.88 | |
| eeeeeee eeeeee | M8M8MMe | 8e [Meeeeeeee ee Meeee 8 (Me…Me)] | 8.8.8 |
| α-eeeeeeeeeeee | |
8.8.88 | |
| eeeeeeeee eeeeee | M8M8MM | 8e [Meeeeeeee ee Meeee 8 (Me…Me)] | 8.8.8.8.8, 8.8.8 |
| eeeeeeeeeeeee eeee eeeeeeeee | |
88 (Meee Meeeee—Meeeeeeeee Meeee: M—M≡M, M=M=M, M8M=M, MM8) | 88.88.8 |
| eeeeeeeeeeeee eeee eeeeeee eeeeeeee | |
88.88.8 | |
| eeeeeeeeeeeeeeeeeeeeee | |
88.88.8 | |
| eeeeeeeeeeeeeeeeeeee eeeeeeeee | |
88.88.88 | |
| eeeeeeeeeeeeeeeeeee eeee eeeeeee eeeeeeee | |
88.88.88 | |
| eeeeeeeeeeeeee-, eee eeeeeeeeeeeeeeeeeeeeeeeeeeeee | |
88.88.88 | |
| eeeeeeeeeeeee eeee eeeeeeeeeee | |
88.88.88 | |
| 8-eeeeeeeeeeeee eeeee | |
88e (Meeee Meeeee—Meeeeeeeee Meeee: Meee Meeeeee; Meeeeeeeee Meeee eee Meee Meeee) | 88.8.8 |
| 8-eeeeeeeeeeeee eeeee | |
88.8.88.8.8 | |
| 8-eeeeeeeeeeeee eeee eeeeee | |
88e [Meeee Meeeee—Meeeeeeeee Meeee: Meeeee eee Meeeeeee; Meeeee Meeee eee M(MM)MM Meeeeeeee; M(MM)M, M = M, Me, Me] | 88.8.88 |
| 8-eeeeeeeeeeeee eeee eeeeee | |
88.8.88.8.8 | |
| α,M-eeeeeeeeeee eeeeeeeeeee | |
88 (Meeee Meeeee—Meeeeeeeee Meeee: Meeeee eee Meeeeeeeeee; Meeeeeee; Meeeeee) | 88.8.8 |
| β,M-eeeeeeeeeee eeeeeeeeeee | |
88.8.8 | |
| eeeee eeeeee | |
88 (Meeee Meeeee—Meeeeeeeee Meeee: Meee-, Meeeee, eee Meeeeeeeeeeeeeeee Meeee eee Meeeeeeeeee; Meeeee Meeee eee Meeeeeeeeee; Meeee Meee Meeeeeeeeee) | 88.8.8 |
| 8-eeeeeeeeeeeeee | |
88 (Meeeeeeee) | 88.8.8 |
| α-eeeee eeeeeee | |
88 (Meeeeee) | 88.8.8 |
| M/M-eeeeeee | |
88 (Meeeeee: M/M, M/M, M/M, eee M/M eee Meeeee Meeeeeeeee Meeeeeeee) | 88.8.8, 88.8.8, 88.8, 88.8.8, 88.8.8, 88.8, 88.8.8 |
| eeeeee(eee)eeeeeeeee eeeee | |
88e [Meeee—M (M = Mee, M, M, Me,Me)] | 88.88.8.8.8 |
| eeeee(eeee)(eee)eeeeeeeee eeeee | |
88.88.8.8.8 | |
| eeeee(eeee)eeeeeeeee eeeee | |
88.88.8.8.8 | |
| eeeeeeeeee | |
88e [Meeee—M (M = M, M)] | 88.88 |
| eeeeeeeeeeee eeeee | |
88.88 | |
| M-eeeeeeeeeeeeee | |
88.88 | |
| M-eeeeeeeeeeeeeeeeee | |
88.88 | |
| eeeeeeeeeeeeee | |
88.88 | |
| eeeeee eeeeeeeeee | |
88.88 | |
| β-eeeeeeeeeeee | |
88 (Meeeeeee) | 88.88 |
| β-eeeeee-, β-eeeee-, eee β-eeeeeeeeee | |
88 (Meeeeeee, Meeeeee, eee Meeeee) | 88.8.8.8.88, 88.8.8.8, 88.8.8.8.8, 88.8.8.8, 88.8.8.8.8, 88.8.8.8 |
| β-eeeee eeeeeeee | |
88 (Meeeeeee) | 88.88.8.8.8, 88.88.8.8.8, 88.88.8.8.8, 88.88.8.8.88 |
| γ-eeeee eeeeeeee | |
88.88.8.8.8–88.88.8.8.8 | |
| β-eeeee eeeeee | |
88 (Meeeee, Meeeeeee, eee Meeeeeeee) | 88.8.8.8.8, 88.8.8.8 |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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