39563-54-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 3909, 1981 DOI: 10.1021/jo00332a030

InChI:InChI=1/C11H23Br/c1-3-4-5-6-7-8-9-10-11(2)12/h11H,3-10H2,1-2H3

Upstream product

• 1653-30-1 undecan-2-ol 
• 58856-08-9 2-methylselenoundecane 
• 112-31-2 caprinaldehyde 
• 112-12-9 methyl nonyl ketone 
• 68141-17-3 2-methylundecanal dimethyl acetal 
• 286408-72-8 2,3-dimethyl-2-(1-methoxy-2-methylundecyl)peroxybut-3-ene 
• 74036-98-9 1,10-dibromoundecane 
• 61539-80-8 (undecane-2-seleninyl)-benzene 
• 58856-10-3 2-methaneseleninyl-undecane 
• 821-95-4 1-undecene 

Downstream Products

• 13490-36-3 3-methyldodecanoic acid 
• 1120-21-4 n-Undecane 
• 124-18-5 decane 
• 928-23-4 2--ethanthioschwefelsaeure 
• 6345-92-2 (1-methyl-decyl)-malonic acid diethyl ester 

Relevant academic research and scientific papers

Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes

A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.

Nickel-catalyzed coupling reactions of alkyl electrophiles, including unactivated tertiary halides, to generate carbon-boron bonds

Through the use of a catalyst formed in situ from NiBr2? diglyme and a pybox ligand (both of which are commercially available), we have achieved our first examples of coupling reactions of unactivated tertiary alkyl electrophiles, as well as our first success with nickel-catalyzed couplings that generate bonds other than C-C bonds. Specifically, we have determined that this catalyst accomplishes Miyaura-type borylations of unactivated tertiary, secondary, and primary alkyl halides with diboron reagents to furnish alkylboronates, a family of compounds with substantial (and expanding) utility, under mild conditions; indeed, the umpolung borylation of a tertiary alkyl bromide can be achieved at a temperature as low as -10 °C. The method exhibits good functional-group compatibility and is regiospecific, both of which can be issues with traditional approaches to the synthesis of alkylboronates. In contrast to seemingly related nickel-catalyzed C-C bond-forming processes, tertiary halides are more reactive than secondary or primary halides in this nickel-catalyzed C-B bond-forming reaction; this divergence is particularly noteworthy in view of the likelihood that both transformations follow an inner-sphere electron-transfer pathway for oxidative addition.

Intramolecular homolytic displacements. 30. Functional decarbonylative transformations of aldehydes via homolytically induced decomposition of unsaturated peroxyacetals

Homolytically induced decompositions of unsaturated peroxyacetals, synthesized from aldehydes, gave alkoxyalkoxyl radicals that yielded alkyl radicals by rapid β-scission. The latter radicals could react with several types of "transfer agents" to smoothly bring about homolytic decarbonylative functional group transformations of aldehydes into halides, hydrocarbons, xanthates, alkanenitriles, 2-alkyl-3-chloromaleic anhydrides, 1-phenylalk-1-ynes, and ethyl 2-alkylpropenoates.