Reductive lithiation of alkyl phenyl sulfides in diethyl ether. A ready access to α,α-dialkylbenzyllithiums

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5633-5635

  Screttas, Constantinos G ^a   Heropoulos, Georgios A ^a   Micha Screttas, Maria ^a   Steele, Barry R ^a   Catsoulacos, Dimitrios P ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

Author keywords

Lithiation; Magnesium alkoxide; Radical anion; Reduction; Thioethers

Indexed keywords

ALKYL GROUP; ETHER; LITHIUM DERIVATIVE; MAGNESIUM DERIVATIVE; NAPHTHALENE; ORGANOLITHIUM COMPOUND; PHENYL GROUP; REAGENT; SOLVENT; SULFIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; LITHIATION; MOLECULAR STABILITY; REACTION ANALYSIS; REDUCTION; STORAGE;

EID: 0038166703     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01371-6     Document Type: Article

References (19)

1. Cohen T., Kreethadumrongdat T., Liu X., Kulkarni V. J. Am. Chem. Soc. 123:2001;3478.
2. For reviews, see: (a) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2002, 8, 2574; (b) Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225; (c) Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152.
3. For reviews, see: (a) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2002, 8, 2574; (b) Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225; (c) Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152.
4. For reviews, see: (a) Yus, M.; Herrera, R. P.; Guijarro, A. Chem. Eur. J. 2002, 8, 2574; (b) Ramon, D. J.; Yus, M. Eur. J. Org. Chem. 2000, 225; (c) Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 152.
5. Screttas C.G. J. Chem. Soc., Chem. Commun. 1972;752.
6. Screttas C.G., Micha-Screttas M. J. Org. Chem. 43:1978;1064.
7. Screttas C.G., Micha-Screttas M. J. Org. Chem. 44:1979;713.
8. A report from this laboratory (Ref. 5) that cumyl phenyl sulfide gives an 80% yield of cumyllithium, was in error due to the erroneous transfer of data from the Table of alkylsodium and alkylpotassium compounds to that for alkyllithiums. See also Ref. 7.
9. Kulkarni V., Cohen T. Tetrahedron. 56:1997;12089.
10. 2 was also used, the volume of water added after the carboxylation step was increased to 250 mL and then subsequently reduced as above in order to ensure complete removal of the 2-ethoxyethanol formed by hydrolysis of the alkoxide.
11. Brown H.C., Kim C.J. J. Am. Chem. Soc. 90:1968;2082.
12. Levin G., Holloway B.E., Szwarc M. J. Am. Chem. Soc. 98:1976;5706.
13. Screttas C.G. J. Chem. Soc., Chem. Commun. 1972;869.
14. Wei X., Johnson P., Taylor R.J.K. J. Chem. Soc., Perkin Trans. 1. 2000;1109.
15. 2), 6.99-7.30 (10H, 2Ph).
16. Screttas C.G., Micha-Screttas M. Organometallics. 3:1984;904.
17. Screttas C.G., Steele B.R. J. Org. Chem. 54:1989;1013.
18. Salteris C.S., Kostas I.D., Micha-Screttas M., Heropoulos G.A., Screttas C.G., Terzis A. J. Org. Chem. 64:1999;5589.
19. Kostas I.D., Screttas C.G. J. Org. Chem. 62:1997;5575.