Tetrahedron Letters

Synthesis of 1-methyl-4-alkyl-1, 3-diacetylenes. Prototropic rearrangement in 1-alkyl-1, 3-diacetylenes

MJ Dabdoub, VB Dabdoub, EJ Lenardao

Index: Dabdoub, Miguel J.; Dabdoub, Vania B.; Lenardao, Eder J. Tetrahedron Letters, 2001 , vol. 42, # 10 p. 1807 - 1809

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Citation Number: 18

Abstract

Treatment of 2-methyl-2-hydroxy-6-alkyl-3, 5-diacetylenes with powdered NaOH was used for the synthesis of terminal 1-alkyl-1, 3-butadiynes that can be isolated (54–97%) or used in situ. In an attempt to increase the yields of some of the obtained products, different experimental conditions were studied and we found that by using CTAB as a catalyst, a prototropic rearrangement was promoted to afford the 1-methyl-4-alkyl-1, 3-diacetylenes ...