1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is HC2C4H9. A colorless liquid, it is one of three isomers of hexyne.[1] It is used as a reagent in organic synthesis.

Synthesis and reactions

1-Hexyne can be prepared by the reaction of monosodium acetylide with butyl bromide:[1]

NaC2H + BrC4H9 → HC2C4H9 + NaBr

Its reactivity illustrates the behavior of terminal alkylacetylenes. The hexyl derivative is common test substrate because it is conveniently volatile. It undergoes deprotonation at C-3 and C-1 with butyl lithium:

HC2C4H9 + 2 BuLi → LiC2CH(Li)C3H7 + 2 BuH

This reaction allows alkylation at the 3-position.[2]

Catechol borane adds to 1-hexyne to give the 1-hexenyl borane. [3]

1-Hexyne reacts with diethyl fumarate to produce n-hexylsuccinic acid.[4]

See also

References

  1. ^ a b Kenneth N. Campbell, Barbara K. Campbell (1950). "n-Butylacetylene". Organic Syntheses. 30: 15. doi:10.15227/orgsyn.030.0015.
  2. ^ A. J. Quillinan, F. Scheinmann (1978). "3-Alkyl-1-Alkynes Synthesis: 3-Ethyl-1-Hexyne". Organic Syntheses. 58: 1. doi:10.15227/orgsyn.058.0001.
  3. ^ Norio Miyaura Akira Suzuki (1990). "Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene". Organic Syntheses. 68: 130. doi:10.15227/orgsyn.068.0130.
  4. ^ Hogsed, M. J.; Lindsey, R. V. (1953-10-01). "The Reaction of 1-Hexyne and Diethyl Fumarate". Journal of the American Chemical Society. 75 (19): 4846–4847. doi:10.1021/ja01115a517. ISSN 0002-7863.
Allikas: Https://en.wikipedia.org/wiki/1-Hexyne
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