1145-91-1

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 3234-51-3 1,1-dibromo-2-phenylcyclopropane 
• 21019-54-5 phenyl[(1S,2S)-2-phenylcyclopropyl]methanone 
• 1145-92-2 (1SR,2SR)-phenyl(2-phenylcyclopropyl)ketone 
• 108-98-5 thiophenol 
• 108401-93-0 E-1-bromo-1-benzoyl-2-phenylcyclopropane 
• 100-52-7 benzaldehyde 
• 54561-18-1 ((1S,2R)-1-Bromo-2-phenyl-cyclopropyl)-phenyl-methanol 
• 1774-47-6 trimethylsulfoxonium iodide 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 100-42-5 styrene 
• 3282-32-4 2-diazo-acetophenone 
• 32523-76-5 cis-1-bromo-2-phenylcyclopropane 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Intermolecular asymmetric cyclopropanation with diazoketones catalyzed by chiral ruthenium porphyrins

The asymmetric addition of diazoacetophenone to styrene derivatives to give optically active cyclopropyl ketones (ee up to 86%) was carried out by using chiral ruthenium porphyrins as homogeneous catalysts.

Hantzsch Ester-Mediated Photochemical Transformations in the Ketone Series: Remote C(sp3)-H Arylation and Cyclopentene Synthesis through Strain Release

A metal-free Hantzsch ester-mediated synthesis of cyclopentenylketones as well as O-hetarylketones starting from ketocyclopropanes under eco-friendly conditions was developed. The versatility of the developed conditions is shown by reacting ketocyclopropanes in both a formal [3 + 2] cycloaddition with terminal alkynes (further investigated using theoretical calculations) and a radical C-C-coupling with cyanopyridines. The newly developed methodologies were later on utilized as a downstream reaction for photogenerated cyclopropanes combining UV and visible light photochemistry. Following this procedure, a UV-driven Norrish-Yang-type reaction induces the ring strain of the intermediates, which serves as activation energy for the subsequent ring transformation.

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Asymmetric intermolecular cyclopropanation of alkenes by diazoketones catalyzed by Halterman iron porphyrins

The asymmetric addition of diazoacetophenone to styrene derivatives to give optically active cyclopropyl ketones (ee up to 80%) was carried out using chiral iron porphyrins as homogeneous catalysts. Intermolecular N-H functionalization of anilines by mean

Catalytic reactions of carbene precursors on bulk gold metal

Bulk gold metal powder, consisting of particles (5-50 μm) much larger than nanoparticles, catalyzes the coupling of carbenes generated from diazoalkanes (R2C=N2) and 3,3-diphenylcyclopropene (DPCP) to form olefins. It also catalyzes cyclopropanation reactions of these carbene precursors with styrenes. The catalytic activity of the gold powder depends on the nature of the gold particles, as determined by TEM and SEM studies. The reactions can be understood in terms of mechanisms that involve the generation of carbene R2C: intermediates adsorbed on the gold surface.

Stereoselective preparation of cyclopropylmagnesium reagents via a Br-Mg exchange using i-PrMgCl·LiCl in the presence of dioxane

The reaction of various cyclopropyl bromides with i-PrMgCl·LiCl in THF-dioxane provides the corresponding magnesiated cyclopropane reagents with complete retention of configuration. Georg Thieme Verlag Stuttgart.

Photochemical synthesis of highly functionalized cyclopropyl ketones

A series of di- and trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3. The irradiation of 3 and 5 must be performed in the presence of an acid scavenger (1-methyl-1H-imidazole) to obtain the cyclopropanes 11 in good yields. The synthetic efficiency of the method was, among other things, demonstrated by the preparation of a highly strained bicyclo[2.1.0]pentane 11i in good yield. The mechanism of the photochemical cyclization was investigated by means of photokinetic measurements, as well as by quantum-chemical calculations. It was shown that the presence of the leaving group substantially influences all steps of the photochemical reaction cascade. The X-ray crystal structures of 11j and exo-11k were also determined.

A new photochemical route to cyclopropanes

Especially highly substituted cyclopropanes can be produced with a new photochemical approach. Starting with aromatic ketones that bear a leaving group adjacent to the carbonyl carbon atom, photolysis leads to the formation of 1,3-diradicals, which efficiently cyclize to cyclopropanes (see scheme; Ms=MeSO2).

Reversible cyclopropyl ring opening of 1-aroyl-2-phenylcyclopropane radical anions. Determination of the ring opening and closure rates of the intermediate ketyls

The phenylcyclopropylketyl ring opening has been used as a mechanistic probe for the detection of radical intermediates. The reaction is of limited use since the ring-opening reaction is reversible. 1-Benzoyl-2-phenylcyclopropane (II) was considered to be

REACTION OF α-BROMOCYCLOPROPYL PHENYL KETONES WITH LITHIUM THIOPHENOLATE BY A MECHANISM OF "LATENT" NUCLEOPHILIC SUBSTITUTION AT THE HALOGEN ATOM

The reaction of E-1-benzoyl-1-bromo-2-phenylcyclopropane with lithium thiophenolate in THF leads to the formation of E-1-benzoyl-2-phenyl-1-phenylthiocyclopropane.Phenyl α-phenylthiocyclopropyl ketones are also produced with good yields by the action of s