Ishikawa’s Reagent

Reaction of perfluoropropene with diethylamine yields (F)-fluoroenaminc 3 and fluoro-alkylamine 4 in a 1 1 or 3 1 mixture (depending on the reaction conditions used). This mixture is known as Ishikawa s reagent and can be used (without separation) for the transformation of alkyl alcohols to fluoroalkanes (see Vol. ElOb/Part 1. p99).218... 

A -methylfonnanilides 16 to tetramers 17, in addition to other products such as isatins (Scheme 4, equation 1) [11]. Ishikawa s team applied an abnormal Bischler-Napieralski cyclization of Vilsmeier reagents to give unusual azazulenes... 

Ishikawa S, Manabe K (2007) Ortho-selective cross coupling of dibromophenols and dibromoanilines with Grignard reagents in the presence of palladium catalysts bearing hydrox-ylated oligoarene-type phosphine. Chem Lett 36 1304-1305... 

Ishikawa S, Manabe K (2011) Hydroxyiated terphenylphosphine ligands for palladium-catalyzed ort/io-selective cross-coupling of dibromophenols, dibromoanilines, and their congeners with Grignard reagents. Tetrahedron 67 10156-10163... 

Both aliphatic and aromatic carboxylic acids are converted to their fluorides by FAR [78, 79, by the Ishikawa reagent [S/], and by fluoroaminosulfuranes such as DAST [128, 166] and its analogues [128]... 

Simple primary alcohols generally give high yields of the expected fluoro compounds when treated with the Yarovenko reagent, 2-chloro-Ar,/V-diethyl-l,1,2-trifluoroelhylamine (1). or the Ishikawa reagent, A W-diethyl-l.l. S.S-hexafluoropropylamine (2) examples are given in... 

Succinimidyl-4-(N-maleimidomethyl)cyclohexane-l-carboxylate (SMCC) is a heterobifunctional cross-linker with significant utility in cross-linking proteins, particularly in the preparation of antibody-enzyme and hapten-carrier conjugates (Hashida and Ishikawa, 1985 Dewey et al., 1987). The NHS ester end of the reagent can react with primary amine groups on proteins to form stable amide bonds. The maleimide end of SMCC is specific for coupling to sulfhydryls when the reaction pH is in the range of 6.5-7.S (Smyth et al., 1964) (Fig. 158). 

Tsunoda S, Ishikawa T, Yamamoto Y (1999). Enhanced antitumor potency of polyethylene glycolylated tumor necrosis factor-alpha A novel polymerconjugation technique with a reversible amino-protective reagent. /. Pharmacol. Exp. Ther. 290 368-372. 

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