73089-99-3

Upstream product

• 699-61-6 1-oxaspiro[4.5]decan-2-one 
• 23708-47-6 1,4-bis(bromomagnesium)butane 
• 33448-80-5 1-oxaspiro[4.4]nonan-2-one 
• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 70430-95-4 1-(1-hydroxy-cyclopentylethynyl)-cyclohexanol 
• 108-94-1 cyclohexanone 
• 114694-23-4 1-(2-Phenylsulfanyl-ethyl)-cyclopentanol 
• 120-92-3 cyclopentanone 
• 195154-34-8 1-(2-Phenylsulfanyl-ethyl)-cyclohexanol 
• 1940-19-8 1-vinylcyclohexanol 
• 3859-35-6 1-vinyl-1-cyclopentanol 
• 6963-45-7 1-(3-hydroxypropyl)-cyclohexanol 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Relevant academic research and scientific papers

Synthesis and Applications of Tetrahydrofuran-Stable Substituted (3-Lithioxyalkyl)- and (4-Lithioxyalkyl)lithiums, Modified with Magnesium 2-Ethoxyethoxide

Substituted hydroxyalkyl phenyl sulfides 3 have been synthesized from the corresponding allylic or homoallylic alcohols 2. Regiospecific cleavage of the C - SPh bond of the sulfides 3 by lithium dispersion in tetrahydrofuran (THF) led to the synthesis of substituted (3-lithioxyalkyl)- and (4-lithioxyalkyl)lithiums 4, most of which share the ω carbon with a carbocyclic ring. The organolithiums were modified with magnesium 2-ethoxyethoxide in order to suppress their reactivity toward THF cleavage, thus offering the advantage of preparing storable ethereal solutions of certain types of (lithioxyalkyl)lithiums. This strategy appears to be of rather broad scope. The functionalized organolithiums prepared in this way react normally with electrophilic reagents with yields in the range 35-55%. Thus, carboxylations of 4 yielded lactones 5, some of which are natural products, while reactions of 4 with benzophenone and cyclic ketones yielded 1,4- and 1,5-diols 6 and 7, respectively.

One-Step Annelation. A Convenient Method for the Preparation of Diols, Spirolactones, and Spiroethers from Lactones

1-(ω-Hydroxyalkyl)cyclopentanols and -cyclohexanols were prepared in one step in high yields from butane-1,4-diyl- and pentane-1,5-diylmagnesium dibromides and lactones in tetrahydrofuran.This method was found to be general and applicable to lactones of any size (β, γ, δ, and ε) and structure whether aliphatic, aromatic, bicyclic, or spirocyclic.Evidently important steric hindrance close to the carbonyl group prevents annelation and attack on the second nucleophilic center of the Grignard reagent.Furthermore, in the case of oxetan-2-one one obtains, in additionto the corresponding diol, products resulting from scission of the C-O bond.The diols by appropriate transformation afford new routes to spirolactones and spiroethers.