Darstellung von 1,2,3,4-Tetramethyl-1,4-diboracyclohexen-2 und Umlagerung zum 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborol / Synthesis of 1,2,3,4-Tetramethyl-1,4-diboracyclohexene-2 and Rearrangement to 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborole

J.-K. Uhm; H. Römich; H. Wadepohl; W. Siebert

doi:10.1515/znb-1988-0312

Open Access Published by De Gruyter June 2, 2014

Darstellung von 1,2,3,4-Tetramethyl-1,4-diboracyclohexen-2 und Umlagerung zum 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborol / Synthesis of 1,2,3,4-Tetramethyl-1,4-diboracyclohexene-2 and Rearrangement to 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborole

J.-K. Uhm , H. Römich , H. Wadepohl and W. Siebert

From the journal Zeitschrift für Naturforschung B

https://doi.org/10.1515/znb-1988-0312

Reaction between Cl₂AlCH₂CH₂AlCl₂ and BCl₃ leads to Cl₂BCH₂CH₂BCl_2, in which halogen exchange is achieved by Bl₃ to yield I₂BCH₂CH₂BI₂ (5). Redox reaction between butyne-2 and 5 results in the formation of 1,4-diiodo-2,3-dimethyl-1,4-diboracyclohexene-2 (1a) and iodine. Methylation of 1 a with AlMe₃ leads to the title compound 1 d , established by ¹H, ¹¹B, ¹³C NMR. Heating of 1 d in toluene at 160 °C in a sealed tube results in an intramolecular isomerization to give 1,2,3,4,5-pentamethyl-2,3-dihydro-1,3-diborole (2d) in 90% yield.

: 1,2,3,4-Tetramethyl-1,4-diboracyclohexene-2; 1,2,3,4,5-Pentamethyl-2.3-dihydro-1,3-diborole

Received: 1987-11-24

Published Online: 2014-6-2

Published in Print: 1988-3-1

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Darstellung von 1,2,3,4-Tetramethyl-1,4-diboracyclohexen-2 und Umlagerung zum 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborol / Synthesis of 1,2,3,4-Tetramethyl-1,4-diboracyclohexene-2 and Rearrangement to 1,2,3,4,5-Pentamethyl-2,3-dihydro-1,3-diborole

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