10420-91-4

Usage

Uses

Used in Organic Chemistry:
1,4-Hexadiyne is used as a key component in the production of polymers, coatings, and pharmaceutical intermediates due to its unique chemical properties.
Used in Electronics Industry:
1,4-Hexadiyne is used as a raw material for manufacturing electronic conductive materials, contributing to the development of advanced electronic devices.
Used in Optoelectronics:
1,4-Hexadiyne is used as a precursor in the development of optoelectronic devices, taking advantage of its ability to form stable carbon-rich materials.
Used in Materials Science and Nanotechnology:
1,4-Hexadiyne is used as a valuable building block in the field of materials science and nanotechnology, owing to its potential to form stable carbon-rich materials.
Safety Precautions:
Due to its flammability and potential health hazards, 1,4-Hexadiyne requires proper handling and storage precautions to ensure safety during its use in various applications.

InChI:InChI=1/C6H6/c1-3-5-6-4-2/h1H,5H2,2H3

Upstream product

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Relevant academic research and scientific papers

Spectroscopy and photochemistry of triplet methylpentadiynylidene (Me-C≡C-C-C≡C-H)

Triplet carbene methylpentadiynylidene, MeC5H (1), was investigated in cryogenic matrices by IR, UV/vis, and EPR spectroscopy. Broadband irradiation (λ > 497 nm) of the isomeric diazo compounds, 1-diazo-hexa-2,4-diyne (2) or 2-diazo-hexa-3,5-diyne (3), generates tripletcarbene 1. EPR spectra yield zero-field splitting parameters (/D/hc/) 0 .62 cm-1, /E/hc/ -1), which are typicalfor a triplet carbene with axial symmetry. The electronic spectrum of t riplet 1 is characterized by a weak absorption in the near-UV and visible region (350-430 nm) with vibronic progressions corresponding to excitations of the acetylenic stretching and the terminal C≡C-H bending modes. Chemical trapping of triplet 1 in an O2-doped matrix affords carbonyl oxides derived predominantly from attack at C-3. Upon irradiation at λ > 399 nm, triplet 1 undergoes photochemical 1,2-hydrogen migration to form hex-1-ene-3,5-diyne (6).

Reactions retrodieniques. XII. Cycloreversions et rearrangements d'ethano-9,10 dihydro-9-10 anthracenes cyclopropaniques

Five Diels-Alder adducts of anthracene, containing respectively the spiro cyclopropane (3), vinylcyclopropane (4), allenylcyclopropane (5) and methylenecyclopropane systems (6 and 7) have been synthesized and their flash thermolytic behaviour investigated.Whereas the adduct 3 undergoes exclusively a retro-Diels-Alder cleavage leading to methylenecyclopropane, two types of rearrangements are observed, owing to their structure, as predominant reaction paths with compound 4-7 : the adducts 4 and 5, possessing a vinylcyclopropane unit, almost only rearrange into the corresponding cyclopentene 14 and methylenecyclopentene 15, respectively; on the other hand, the methylenecyclopropene adducts 6 and 7 undergo a more unexpected rearrangement of the anthracenic framework leading to the polycyclic methylenecyclobutanes 19 and 20.The structure proposed for 19 follows unambiguously from its spectral properties and is confirmed by its ozonolysis yielding the cyclobutanone 21.In the same way, the retro-Diels-Alder cleavage of the adducts 4-7, also observed as a minor reaction path (10-40percent), is followed by the isomerization of the firstly obtained cyclopropanic cumulenes, leading to 1,4-hexadiyne (from 5), dimethylenecyclopropane (from 6), or 1-hexen-4-yne and ethylidenemethylenecyclopropane (from 7).