Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride. Part 2: The Friedel-Crafts allylation and cyclopropylation of electron-rich aromatic compounds

Tetrahedron Letters

Volumn 47, Issue 22, 2006, Pages 3777-3780

  Kirihara, Masayuki ^a   Noguchi, Takuya ^a,b   Kakuda, Hiroko ^b   Akimoto, Tatsuhiro ^a   Shimajiri, Akihiro ^a   Morishita, Minori ^a   Hatano, Akihiko ^a   Hirai, Yoshiro ^b  

^a SHIZUOKA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

Cyclopropyl silyl ether; Diethylaminosulfur trifluoride; Friedel Crafts allylation; Friedel Crafts cyclopropylation

Indexed keywords

AROMATIC COMPOUND; DIETHYLAMINOSULFUR TRIFLUORIDE; ETHER DERIVATIVE; FLUORIDE; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ARTICLE; CHEMICAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 33646116802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.03.120     Document Type: Article

References (8)

1. Reviews:. Murai S., Ryu I., and Sonoda N. J. Organomet. Chem. 250 (1983) 121-133
2. Kuwajima I., and Nakamura E. Top. Curr. Chem. 155 (1990) 1-39
3. Ryu I., and Murai S. In: deMeijere A. (Ed). Methoden der Organisches Chemie (Houben-Weyl) Vol. E17 (1997), Georg Thieme, New York 1985-2040
4. Kulinkovich O.G. Chem. Rev. 103 (2003) 2597-2632
5. Kirihara M., Kambayashi T., and Momose T. Chem. Commun. (1996) 1103-1104
6. Kirihara M., Kakuda H., Tsunooka M., Shimajiri A., Takuwa T., and Hatano A. Tetrahedron Lett. 44 (2003) 8513-8518
7. To a solution of cyclopropyl silyl ether (0.5 mmol) in a mixed solvent of dichloromethane (2 ml) and furan (0.5, 1.0, or 2.5 mmol) was added DAST (1.5 mmol) at room temperature under an inert atmosphere, and the reaction mixture was stirred for 30 min. The reaction mixture was worked up and purified as described in the general experimental procedure of the text.
8. Hudlicky M. Org. React. (N.Y.) 35 (1988) 513-637