5244-75-7

Upstream product

• 67-56-1 methanol 
• 82517-28-0 cyclobutylphenyldiazomethane 
• 73013-83-9 1-benzyl-1-hydroxycyclobutane 
• 5407-98-7 1-cyclobutyl-1-phenyl-methanone 
• 57718-13-5 (5-bromo-pent-1-ynyl)-benzene 
• 34886-50-5 (5-iodopent-1-yn-1-yl)benzene 
• 7333-63-3 4-bromobutylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 3112-88-7 Benzyl phenyl sulfone 
• 92078-64-3 11-bromo-5-undecyne 
• 5244-80-4 N,N-Dimethyl-α-phenyl-cyclobutyl-methylamin 
• 3666-89-5 cyclobutyl triphenylphosphonium bromide 
• 24463-87-4 (5-chloropent-1-ynyl)benzene 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 93714-50-2 1-Phenylspiro<2.3>hexane 
• 82833-97-4 (1-bromo-1-phenylmethylene)cyclobutane 
• 1198-34-1 2-Phenylcyclopentanone 
• 5244-85-9 (1-Hydroxy-cyclobutyl)-phenyl-methanol 
• 5244-87-1 Essigsaeure-<(1-hydroxy-cyclobutyl)-phenyl-methylester> 
• 87957-41-3 1,1-Dichlor-2-phenylspiro<2.3>hexan 
• 1127971-45-2 C₁₇H₁₅N₃O₂ 
• 1321621-46-8 C₁₁H₁₂O₂ 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 1322744-62-6 C₁₁H₁₃BrO 
• 87957-47-9 1-Chlor-c-2-phenylspiro<2.3>hexan-r-1-carbonsaeure 
• 87957-47-9 1-Chlor-t-2-phenylspiro<2.3>hexan-r-1-carbonsaeure 

Relevant academic research and scientific papers

Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions

We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).

Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions

We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.

Synthesis of multi-substituted cyclobutanes and alkylidenecyclobutanes by the reaction of cyclobutylmagnesium carbenoids with nucleophiles

Treatment of 1-chlorocyclobutyl p-tolyl sulfoxides with Grignard reagents such as ethylmagnesium chloride, isopropylmagnesium chloride, and cyclopentylmagnesium chloride in THF at low temperature gave cyclobutylmagnesium carbenoids in high yields. The gen

Catalytic reduction of phenyl-conjugated acetylenic halides by nickel(I) salen: Cyclization versus coupling

Cyclic voltammetry and controlled-potential electrolysis were employed to study the catalytic reduction of five phenyl-conjugated haloalkynes by nickel(I) salen electro-generated at carbon cathodes in dimethylformamide containing tetramethylammonium tetrafluoroborate. Electrocatalytic reduction of 7-bromo- and 7-iodo-1-phenyl-1-heptyne affords the carbocyclic product, benzylidenecyclohexane, in up to 41 % yield, whereas under similar conditions reduction of 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne gives benzylidenecyclobutane and benzylidenecycloheptane, respectively, in very low yield (≤1 %). Dimers, alkynes, and alkenynes are other products formed from the phenyl-conjugated haloalkynes. Dimers (diphenylalkadiynes) derived from 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne are obtained in yields ranging from 85 to 93 %, whereas 1,14-diphenyltetradeca-1,13-diyne (the dimer produced from 7-halo-1-phenyl-1-heptyne) is found in yields of 45-51 %. To account for the formation of the various products, a mechanistic scheme that involves phenyl-conjugated alkynyl radicals arising from nickel(I) salen catalyzed cleavage of the carbon-halogen bond of each substrate was formulated. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Enantioselective synthesis of 2-aryl cyclopentanones by asymmetric epoxidation and epoxide rearrangement

(Chemical Equation Presented) Optically active epoxides are prepared by the highly enantioselective epoxidation of benzylidenecyclobutanes using a glucose-derived ketone as the catalyst and oxone as the oxidant. A subsequent Lewis acid catalyzed rearrange

Cyclizations during the Grignard Reactions of ω-Bromoalkynes

The Grignard reactions of a number of ω-bromoalkynes have been shown to undergo regioselective cyclizations in certain instances to give the smaller possible carbocycle. These cyclizations are shown to result from two competing processes, whose relative efficiencies depend upon the chain length and the remote substitutent on the acetylene. These are interpreted as a radical cyclization which occurs only during the time the Grignard is being formed from the bromide and an organometallic reaction which slowly transforms the Grignard reagent into its cyclic isomer. The mechanistic details of these transformations are discussed.

Zinc-promoted reactions. 8. The effect of ring strain in the reduction of 1,2-dibenzoylcycloalkanes

Ring cleavage was the main route in the Zn reduction of 1 in neat AcOH, while selective carbonyl reduction predominated in the presence of LiCl. The less strained 2 underwent only carbonyl reduction with Zn/AcOH. The Clemmensen reduction of both 1 and 2 resulted mainly in acyclic products. The unstrained 3 was fairly resistant towards reduction, and did not undergo ring cleavage.

Cyclization of acetylenic alkyllithiums

The scope and limitations of cyclization reactions involving acetylenic alkyllithiums, which were prepared at-78 °C by lithium-iodine exchange between the corresponding iodide and tert-butyllithium in a solution of n-pentane-diethyl ether (3:2 by volume), have been investigated. 4-Pentynyllithiums, 5-hexynyllithiums, and 6-heptynyllithiums bearing a phenyl or trimethylsilyl substituent on the triple bond undergo regiospecific exo-dig cyclization to give 4-, 5-, and 6-membered rings, respectively, bearing an exocyclic lithiomethylene moiety. Cyclization of the analogous alkyl-substituted acetylenic alkyllithiums seems to be confined to the 5-exo mode. The vinyllithium products of the cyclizations may be trapped by reaction with electrophiles to afford functionalized cycloalkylidene derivatives in good yield. The cyclization reactions were found to be highly stereoselective: intramolecular addition of the C-Li unit to the triple bond to produce 4- or 5-membered rings proceeds in a syn fashion to generate isomerically pure exocyclic vinyllithiums that may be functionalized to give stereoisomerically pure products. At the higher temperatures needed to effect cyclization of 6-heptynyllithiums, the initially formed (Z)-vinyllithium intermediate is isomerized to the more stable E-isomer which, when trapped with an electrophile, affords stereoisomerically pure product formally derived from anti addition to the triple bond.

1,2-Hydrogen migration and alkene formation in the photoexcited states of alkylphenyldiazomethanes

Laser flash photolysis of alkylphenyldiazomethanes in the presence of pyridine produces easily detected ylides. The data indicate that photolysis of alkylphenyldiazomethanes leads to both carbene formation and direct formation of rearrangement products which do not derive from relaxed carbene intermediates.