4911-60-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 4740, 1980 DOI: 10.1021/jo01311a037

InChI:InChI=1/C8H14/c1-5-6-7-8(2,3)4/h5H2,1-4H3

Upstream product

• 17553-39-8 2-Chlor-2-methyl-3-hexin 
• 29022-23-9 2-methoxy-2-methyl-hex-3-yne 
• 75-16-1 methylmagnesium bromide 
• 74-96-4 ethyl bromide 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 2586-89-2 hept-3-yne 
• 3287-02-3 4-(phenylethynyl)toluene 
• 928-49-4 hex-3-yne 
• 77-78-1 dimethyl sulfate 
• 13994-33-7 4-methyl-1,2,3-pentatriene 
• 90822-58-5 mer-Mo(CC(CH₃)3)(OCH(CF₃)2)(1,2-dimethoxyethane) 
• 5075-33-2 2-methyl-3-hexyn-2-ol 

Relevant academic research and scientific papers

Polylithiumorganic compounds - 23. 1: 3,4-dilithio-1,2-butadienes by addition of lithium metal to 1,4-unsymmetrically substituted butatrienes

The synthesis of the highly reactive 1,4-unsymmetrically substituted butatrienes 12a-c is described. When employing a strict synthetic protocol, these alkatrienes react with lithium metal to 3,4-dilithio-1,2-butadienes 20a-c as stable intermediates. The structure of 20 is supported by IR and NMR spectroscopic evidence. The same dianionic intermediate can be prepared in one case by double deprotonation of the 1,2-butadiene 19. Upon derivatization, either 3,4-disubstituted 1,2-butadienes 24, 2,3-disubstituted 1,3-butadienes 25, or 1,4-disubstituted 2-butynes 26 are formed, depending on the nature of the electrophile employed. Copyright

Stereoselective synthesis of vicinal dilithioalkenes by addition of lithium metal, to carbon-carbon triple bonds

The reaction of various cyclic and acyclic alkynes with lithium dust (2% sodium) to form vicinal dilithioalkenes has been investigated. Aliphatic alkynes, e.g. 3-hexyne (27a), exclusively afford the corresponding (E)-dilithioalkenes, insoluble solids which are stable at room temperature and allow access to a variety of tetrasubstituted olefins in acceptable yields.

THE ELECTRON SPIN RESONANCE SPECTRA OF THE ANNULENE (CYCLOBUTADIENE) RADICAL CATIONS, R4C4+.

A series of simple (R=R') and mixed (RR') cyclobutadiene radical cations, R2R'2C4+., have been prepared by photolysis of the alkynes, RCCR' or of mixtures of the alkynes RCCR and R'CCR', in dichloromethane in the presence of aluminium chloride, and the e.s.r. spectra have been recorded.The magnitude of the 13C hyperfine coupling in Et4C4+. confirms that it is a ?-radical, with no evidence for out-of-plane or in-plane (Jahn-Teller) distortion.The values of a(Hβ) for the radicals (RCH2)4C4+. and (RCH2)2R'2C4+. indicate that, as the bulk of the alkyl substituents increases, the group R is pushed out of the plane of the ring.Some unusual temperature effects on a(Hβ) are ascribed to interaction of the radical cation with the solvent or with the counterion.As the bulk of the alkyl groups increases, the g-value decreases from 2.0030 to about 2.0022. cis- and trans-Isomers of the radicals Me2tBu2C4+., Et2tBu2C4+., iBu2tBu2C4+., and propably Me2Et2C4+. have been identified, and the spectra of cis- and trans-Me2tBu2C+. are analysed in terms of breaking of the degeneracy of the molecular orbitals of the cyclobutadiene system by differential electron release by the alkyl groups (tBu > Me).