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Communication

Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols

Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, Prospekt Oktyabrya, 141, 450075 Ufa, Russia
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Author to whom correspondence should be addressed.
Academic Editor: Stefano D’Errico
Molbank 2022, 2022(2), M1379; https://doi.org/10.3390/M1379
Received: 28 April 2022 / Revised: 30 May 2022 / Accepted: 31 May 2022 / Published: 4 June 2022
(This article belongs to the Section Organic Synthesis)
Aliphatic thiols are in high demand in materials chemistry. Herein, a synthesis of thio-derivatives of 1-hexene vinylidene dimer is described. The approach, based on a hydroalumination reaction with further replacement of the organoaluminum function with sulfur using thiourea or dimethyl disulfide, provides anti-Markovnikov products, 2-butyloctane-1-thiol or 5-(methylsulfanylmethyl)undecane, in moderate yields. The reaction of a vinylidene dimer with phosphorus pentasulfide in the presence of catalytic amounts of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) selectively gives the Markovnikov product, 5-methylundecane-5-thiol, with a yield of up to 77%. View Full-Text
Keywords: vinylidene dimers; phosphorus pentasulfide; thiourea; dimethyl disulfide; thiols vinylidene dimers; phosphorus pentasulfide; thiourea; dimethyl disulfide; thiols
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MDPI and ACS Style

Kovyazin, P.V.; Bikmeeva, A.K.; Palatov, E.R.; Parfenova, L.V. Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols. Molbank 2022, 2022, M1379. https://doi.org/10.3390/M1379

AMA Style

Kovyazin PV, Bikmeeva AK, Palatov ER, Parfenova LV. Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols. Molbank. 2022; 2022(2):M1379. https://doi.org/10.3390/M1379

Chicago/Turabian Style

Kovyazin, Pavel V., Almira K. Bikmeeva, Eldar R. Palatov, and Lyudmila V. Parfenova. 2022. "Modification of 1-Hexene Vinylidene Dimer into Primary and Tertiary Alkanethiols" Molbank 2022, no. 2: M1379. https://doi.org/10.3390/M1379

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