A convenient method for the synthesis of 2-arylaziridines from styrene derivatives via 2-arylethenyl(diphenyl)sulfonium salts

Chemistry Letters

Volumn 32, Issue 4, 2003, Pages 392-393

  Matsuo, Jun Ichi ^a,b   Yamanaka, Hiroyuki ^a,b   Kawana, Asahi ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ETHENYL(DIPHENYL)SULFONIUM; AZIRIDINE DERIVATIVE; DIPHENYL(TRIFLUOROMETHANESULFONYLOXY)SULFONIUM; STYRENE DERIVATIVE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038162290     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.392     Document Type: Article

References (17)

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14. The use of 2-arylethenyl(dimethyl)sulfonium salts instead of 2-arylethenyl(diphenyl)sulfonium salts resulted in N-methylation of primary amines to afford 2-arylethenyl methyl sulfides.
15. a's of conjugate acids of aziridines are usually in the range of 8-9.5, whereas they are ca. 10 for primary amines. See: P. E. Fanta, in "Heterocyclic Compounds with Three- and Four-Membered Rings," ed. by A. Weissberger, John Wiley and Sons, New York (1964), Part 1, p 527.
16. 2O, was added to a solution of the sodium salt of diethyl malonate (1.2 equiv.) or ethyl cyanoacetate (1.2 equiv.) in THF. The reaction mixture was stirred at rt for 2h, and diethyl 2-phenyl-1,1-cyclopropanedicarboxylate (77%) or ethyl 1-cyano-2-phenylcyclopropanecarboxylate (76%) was obtained respectively. Similarly, diphenyl[(E)-2-phenylethenyl]sulfonium triflate also reacted with the sodium salt of diethyl malonate to give diethyl 2 phenyl-1,1-cyclopropanedicarboxylate (76%, 2 steps from styrene). Preparation of cyclopropanes via sulfonium salts had already been reported, see: a) J. Gosselck, L. Béess, and H. Schenk, Angew. Chem., 78, 606 (1966). b) J. Gosselck, H. Ahlbrecht, F. Dost, H. Schenk, and G. Schmidt, Tetrahedron Lett., 9, 995 (1968).
17. 2O, was added to a solution of the sodium salt of diethyl malonate (1.2 equiv.) or ethyl cyanoacetate (1.2 equiv.) in THF. The reaction mixture was stirred at rt for 2h, and diethyl 2-phenyl-1,1-cyclopropanedicarboxylate (77%) or ethyl 1-cyano-2-phenylcyclopropanecarboxylate (76%) was obtained respectively. Similarly, diphenyl[(E)-2-phenylethenyl]sulfonium triflate also reacted with the sodium salt of diethyl malonate to give diethyl 2 phenyl-1,1-cyclopropanedicarboxylate (76%, 2 steps from styrene). Preparation of cyclopropanes via sulfonium salts had already been reported, see: a) J. Gosselck, L. Béess, and H. Schenk, Angew. Chem., 78, 606 (1966). b) J. Gosselck, H. Ahlbrecht, F. Dost, H. Schenk, and G. Schmidt, Tetrahedron Lett., 9, 995 (1968).