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

✍ Scribed by Miguel J Dabdoub; Vânia B Dabdoub; Eder J Lenardão

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
79 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 in the 62-94% yield range.

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## Abstract magnified image A series of 3‐alkyl/aryl substituted‐6‐((1__H__‐benzo[__d__][1,2,3]triazol‐1‐yl)methyl)‐[1,2,4]triazolo[3,4‐__b__][1, 3,4]thiadizoles **4a**, **4b**, **4c**, **4d**, **4e**, **4f**, **4g**, **4h**, **4i**, **4j**, **4k**, **4l**, **4m** are prepared by the condensation o