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Reference
- Ring-opening reactions of heterocyclic organometallics
- Ring-opening reactions of heterocyclic organometallics. X. Phenyl- and N,N-dimethylaminomethyl-substituted 3-thienyllithium derivatives. Gronowitz, Salo; Frejd, Torbjorn (Chem. Cent., Univ. Lund, Lund, Swed.There are some reagents with their cas registry numbers 61285-25-4 and 5069-26-1 are used in this study.). Acta Chem. Scand., Ser. B, B30(6), 485-90 (English) 1976. CODEN: ACBOCV. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Section cross-reference(s): 23, 29 [2-(Alkylthio)vinyl]acetylenes were prepd. by ring-opening of phenyl substituted 3-thienyllithium derivs. The stability of 2-(N,N-dimethylaminomethyl)-5-methyl-3-thienyllithium (I) towards ring-opening is ascribed to intramol. chelation. On the other hand, 5-(N,N-dimethylaminomethyl)-2-methyl-3-thienyllithium smoothly ring-opened to give 50% (Z)-1-(N,N-dimethylamino)-2-ethylthio-2-hexen-4-yne upon ethylation. .


