25524-42-9

Usage

InChI:InChI=1/C13H26/c1-3-5-7-9-11-13-12-10-8-6-4-2/h9,11H,3-8,10,12-13H2,1-2H3/b11-9-

Upstream product

• 109-72-8 n-butyllithium 
• 42036-78-2 n-octyltriphenylphosphoniumbromide 
• 68-12-2 N,N-dimethyl-formamide 
• 872-05-9 1-Decene 
• 124-19-6 nonan-1-al 
• 21406-61-1 pentyltriphenylphosphonium bromide 
• 546-67-8 lead(IV) tetraacetate 
• 544-63-8 n-tetradecanoic acid 
• 71-43-2 benzene 
• 71-41-0 pentan-1-ol 
• 124-13-0 Octanal 
• 273730-80-6 1-tert-butyl-5-(pentane-1-sulfonyl)-1H-tetrazole 
• 203317-33-3 5-(pentane-1-sulfonyl)-1-phenyl-1H-1,2,3,4-tetrazole 
• 273730-78-2 1-tert-butyl-5-pentylsulfanyl-1H-tetrazole 

Relevant academic research and scientific papers

1-Methyl-1H-tetrazol-5-yl (MT) sulfones in the Julia-Kocienski olefination: Comparison with the PT and the TBT sulfones

The stability and the stereoselectivity of newly prepared n-pentyl 1-methyl-1H-tetrazol-5-yl (MT) sulfone 1a in the Julia-Kocienski reactions were compared with those of the PT sulfone 1b and the TBT sulfone 1c. The improved stability of the anion derived from the n-pentyl MT sulfone 1a enhanced the efficiency of the olefination reactions and gave higher yields of the product alkenes 3 compared with the PT sulfone 1b. Especially high E-selectivity and high yields were obtained from the reaction with aromatic aldehydes and α,β-unsaturated aldehydes. The selectivity of 1a was not so sensitive to the change of base counter ion compared with the PT sulfone 1b. The reaction of the MT sulfones having either ethyl or a longer alkyl chain also gave E-alkenes selectively in high yields.

Stabilization of long-chain intermediates in solution. octyl radicals and cations

The rearrangements of 1-octyl, 1-decyl and 1-tridecyl intermediates obtained from thermal lead(IV) acetate (LTA) decarboxylation of nonanoic, undecanoic and tetradecanoic acid were investigated experimentally through analysis and distribution of the products. The relationships between 1,5-, 1,6- and possibly existing 1,7-homolytic hydrogen transfer in 1-octyl-radical, as well as successive 1,2-hydride shift in corresponding cation have been computed via Monte-Carlo method. Taking into account that ratios of 1,5-/1,6-homolytic rearrangements in 1-octyl- and 1-tridecyl radical are approximately the same, the simulation shows very low involvement of 1,7-hydrogen rearrangement (1,5-/1,6-/1,7-hydrogen rearrangement = 85:31:1) in 1-octyl radical.

Tandem application of C-C bond-forming reactions with reductive ozonolysis

Several variants of reductive ozonolysis, defined here as the in situ generation of aldehydes or ketones during ozonolytic cleavage of alkenes, are demonstrated to work effectively in tandem with a number of C-C bond-forming reactions. For reactions involving basic nucleophiles (1,2- addition of Grignard reagents, Wittig or Horner-Emmons olefinations, and directed aldol reactions of lithium enolates), the one-pot process offers a rapid and high-yielding alternative to traditional two-step protocols.