16609-28-2

Usage

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 3927, 1989 DOI: 10.1016/S0040-4039(00)99286-4

InChI:InChI=1/C10H16/c1-8-5-9(2)7-10(3,4)6-8/h5H,1,6-7H2,2-4H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 186581-53-3 diazomethane 
• 30221-55-7 trimethyl-3,5,5 cyclohexene-2 thione 
• 94925-94-7 3-Hydroxy-1,3,5,5-Tetramethylcyclohexen 
• 31729-70-1 bis(iodozinc)methane 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 4674-21-9 4,6-dibromo-1,2,3,5-tetramethylbenzene 

Relevant academic research and scientific papers

Synthesis of the cyclohexadienyl ruthenium arene complexes [(η5-C6H3Me4)Ru(η6-arene)]+from the dimethyloctadienyl ruthenium chloride[(μ-η3:η3-C10H16)RuCl2]2

Reaction of the readily accessible dimethyloctadienyl ruthenium chloride [(μ-η3:η3-C10H16)RuCl2]2(1) with 1,3,5,5-tetramethylcyclohexadiene and arenes in the presence of TlPF6gives cyclohexadienyl ruthenium arene complexes [(η5-C6H3Me4)Ru(η6-arene)]+in ca. 50% yield (arene = benzene, naphthalene, pyrene, thiophene, ethyl ester of N-acetyl-phenylalanine). In the absence of appropriate arene the major product is the mesitylene complex [(η5-C6H3Me4)Ru(η6-C6H3Me3)]+formed via splitting of the C-Me bond in the 1,3,5,5-tetramethylcyclohexadienyl ligand. The reaction of 1 with p-xylene and TlPF6in the absence of diene gives a methyl-isobutyl substituted pentadienyl complex [(η5-C5H5(iBu)Me)Ru(η6-C6H4Me2)]+(6) via isomerization of the dimethyloctadienyl ligand. The structures of [(η5-C6H3Me4)Ru(η6-naphthalene)]PF6and [6]BPh4were confirmed by X-ray diffraction.

Alkylidenation of carbonyl compounds with gem-dizincioalkanes mediated with titanium dichloride

Olefination of carbonyl compounds with gem-dizincio-alkanes, bis(iodozincio)methane, 1,1-bis(iodozincio)ethane, and bis(bromozincio)methyltrimethylsilane, afforded the corresponding olefins in good to excellent yields.

The reaction of cyclic allylic alcohols with aliphatic alcohols in the presence of cerium(III) chloride

Cyclic secondary and tertiary allylic alcohols react with primary aliphatic alcohols in the presence of cerium(III) chloride heptahydrate to give alkyl allylic ethers. When secondary or tertiary aliphatic alcohols are used 1,3-dienes are obtained from allylic alcohols heaving the 3-methyl-2-en-1-ol moiety (3-8, 13-15).

Regioselectivity and Steric Course of Lewis Acid Promoted Ring Enlargement of Cyclohexadiene Complexes with Carbon Monoxide

Treating the tricarbonyliron complexes 5 and 7 of substituted cyclohexadienes with AlCl3 yields complexes 6, 8, and 9 of seven-membered ring ketones, containing carbon monoxide inserted into one of the double bonds with high regioselectivity depending on the substitution pattern.The mechanism of this ring enlargement is discussed, and an X-ray analysis of 8e is carried out.