868-91-7

Upstream product

• 3282-30-2 pivaloyl chloride 
• 7412-67-1 neopentyl lithium 
• 91337-12-1 methyl-tert-butyl-neopentyl-carbinol 
• 7758-99-8 copper(II) sulfate 
• 1026163-32-5 4-(1,1-dimethylethyl)-4-hydroxy-2,2,5,5-tetramethyl-3-hexyl N-(4-toluenesulfonyl)carbamate 

Downstream Products

• 20818-94-4 dineopentyl-tert-butylcarbinol 
• 40544-02-3 4-Nitro-benzoic acid 1-tert-butyl-1-(4-chloro-phenyl)-3,3-dimethyl-butyl ester 
• 40544-01-2 α-t-butyl-α-neopentylbenzyl p-nitrobenzoate 
• 40544-00-1 4-Nitro-benzoic acid 1-tert-butyl-3,3-dimethyl-1-p-tolyl-butyl ester 
• 40544-03-4 4-Nitro-benzoic acid 1-tert-butyl-3,3-dimethyl-1-(4-trifluoromethyl-phenyl)-butyl ester 
• 40544-09-0 4-Nitro-benzoic acid 1-tert-butyl-1,3,3-trimethyl-butyl ester 
• 34235-21-7 3-(4-chloro-phenyl)-2,2,5,5-tetramethyl-hexan-3-ol 
• 34235-19-3 3-(4-methoxy-phenyl)-2,2,5,5-tetramethyl-hexan-3-ol 
• 190432-52-1 2,2,5,5-tetramethyl-3-m-tolyl-hexan-3-ol 
• 190432-50-9 3-(4-tert-butyl-phenyl)-2,2,5,5-tetramethyl-hexan-3-ol 
• 190432-48-5 3-(3-chloro-4-methoxy-phenyl)-2,2,5,5-tetramethyl-hexan-3-ol 
• 40544-13-6 2,2,5,5-Tetramethyl-3-phenyl-3-hexen 
• 40544-18-1 3-Phenyl-2,2,5,5-tetramethylhexan 
• 20818-92-2 4-tert-butyl-2,2,6,6-tetramethyl-4-(4-nitro-benzoyloxy)-heptane 

Relevant academic research and scientific papers

Sterically congested molecules, 17: Novel syntheses of α,α,β-Tri-tert-butyl compounds

Pivaloin (2), prepared from ethyl pivalate (1) or from dimethyl oxalate (3), reacts with tert-butyllithium by reduction (45% of 10) and addition (45% of 9), whereas the corresponding Barbier variant takes a different course. Productive transformations of the α,α,β-tri-tert-butyl glycol 9 lead to α,β,β-tri-tert-butylethanone (17, overall 4 steps), or α,α,β-tri-tert-butyl-ethene (20, 3 or 4 steps), or α,β,β-tri-tert-butyl-β-hydroxyethanone (19, 3 steps, also by Grignard addition to bipivaloyl 4). Steric congestion is assessed by searches for restricted internal rotation. The alkene 20 and its epoxide 27 are studied with respect to NMR assignments and chemical degradation. VCH Verlagsgesellschaft mbH, 1997.

NOUVELLES METHODES DE DESHALOGENATION ET DE FORMATION D'ETHERS D'ENOL TRIMETHYLSILYLIQUES PAR ACTION DE iPr2NLi SUR QUELQUES α-MONOBROMO- ET α,α'-DIBROMOCETONES

Attempts to prepare 2-bromo-2,4-dimethyl,3-trimethylsiloxy 3-pentene reacting lithium diisopropylamide (LDA) with 2-bromo-2,4-dimethyl-3 pentanone have revealed two new reactions.After a few minutes quantitative yields are obtained of either the dehalogenated ketone (after hydrolysis) or the trimethylsilyl enol ether (after addition of trimethylsilyl chloride).These reactions are general and have been extended to other α-monobromoketones and α,α'-dibromoketones.In the latter case, the reaction is more complex and leads generally to dehalogenation or reduction products.