51708-83-9

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 73, p. 762, 1995 DOI: 10.1139/v95-096

InChI:InChI=1/C9H16/c1-8(2)6-5-7-9(3)4/h1,3,5-7H2,2,4H3

Upstream product

• 77887-46-8 2,2,6,6-tetramethyl-3,4,5,6-tetrahydro-(2H)-pyran 
• 6257-51-8 2,6-dimethyl-2,6-heptanediol 

Downstream Products

• 911798-28-2 1-(3-Chloro-3,7-dimethyl-1-phenyl-oct-7-enyl)-4-methoxy-benzene 
• 75924-59-3 Toluene-4-sulfonic acid (2R,6R)-7-hydroxy-2,6-dimethyl-heptyl ester 

Relevant academic research and scientific papers

STUDIES ON THE CHEMISTRY OF DIOLS AND CYCLIC ETHERS-52. MECHANISM AND STEREOCHEMISTRY OF DEHYDRATION OF OXOLANES TO DIENES

On γ-Al2O3, BPO4 and NaX zeolite, the dehydration of (+/-)-2,2,3,4,5,5-hexamethyloxolane (2) in the vapour phase leads to the formation of 2,3,4,5-tetramethyl-1,5-hexadiene (8) in a slow process, while meso-2,2,3,4,5,5-hexamethyloxolane (3) is converted to 2,3,4,5-tetramethyl-2,4-hexadiene (7) with high selectivity in a fast reaction.These differences in reaction rate and selectivity indicate that the dehydration of 2 takes place by an E2 mechanism.In contrast, the steric strain in 3 results in ring opening by an E1 mechanism.These conclusions are supported by the nonselective transformations of 2,2,5,5-tetramethyloxolane (1) and 2,2,6,6-tetramethyloxane (4), and the dehydration of 1, 2 and 3 in the presence of formic acid in the liquid phase.The experimental observation prove that both the reactivity and the reaction directions in the dehydration of stereoisomeric oxolanes are determined by steric factors.

Studies on the Conversions of Diols and Cyclic Ethers. Dehydration of Alcohols and Diols on the Action of Dimethylsulfoxide

The transformations of 13 alcohols and 13 diols in the presence of a small amount dimethylsulfoxide (1/16 mol) were studied.Relationships were found between the type of the hydroxy compound and the selectivity of the transformation, and conclusions were drawn regarding the transformation mechanism.The ether formation observed with certain alcohols proceeds via a carbenium cation.The reaction conditions applied were found suitable for including water elimination from the ditertiary 1,2- and 1,3-diols (pinacol rearrangement, 1,2-elimination).From the 1,4- and 1,5-diols the corresponding oxacycloalkanes can be obtained in good yield.Cyclodehydration occurs by intramolecular nucleophilic substitution, via a concerted mechanism.The effect of DMSO is excerted directly, and proton-catalysis occurs simultaneously.