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Volumn 22, Issue 51, 1981, Pages 5119-5122

Dipole stabilized a-amino carbanions. III. Metalation-alkylation of indolines, tetrahydroquinolines and n-methylanilines.

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010691990 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)92435-9 Document Type: Article

Times cited : (32)

References (8)

1
- 0000864767
- For Part I, c.f.
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7125
- Meyers¹ Hoeve²

2
- 84918337862
- A.I. Meyers, S. Hellring, and W. Ten Hoeve, previous article in this issue.

3
- 0000801863
- Formylation of t-Butylamine and t-Octylamine1,2
- (1962) The Journal of Organic Chemistry , vol.21 , pp. 4058
- Moffat¹ Newton² Papenmeier³

4
- 84918337861
- This method was used to prepare fonnamidines 1 (bp 100–105°; 0.01 mm) 3 (bp 125°; 0.2 mm; mp 54–56° from pentane), and 5 (bp 60°; 0.03 mm) in 97, 87, and 91% yields, respectively. All three formamidines gave satisfactory elemental analyses.

5
- 84918337860
- Synthesis of 5 was also performed starting with commercially available N-methylformanilide in the manner described for 1 and 3.

6
- 84918337859
- 2O to the ice-cold reaction mixture, stirring at ambient for ~6 h, filtering the salts and washing them with THF. The combined THF solutions were concentrated to give the crude product which was purified by MPLC.

7
- 84982367895
- Umpolung of Amine Reactivity. Nucleophilic ?-(Secondary Amino)-alkylationvia Metalated Nitrosamines
- (1975) Angewandte Chemie International Edition in English , vol.14 , pp. 15
- Seebach¹ Enders²

8
- 0000253140
- For an excellent review on other related methods using dipole-stabilized anions, see
- (1978) Chem. Rev. , vol.78 , pp. 275
- Beak¹ Reitz²

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