59591-01-4

Upstream product

• 37555-48-9 2,2-diphenylcyclopropylmethanol 
• 7746-95-4 2,2-Diphenylcyclopropancarbonsaeurechlorid 
• 7150-12-1 2,2-diphenyl-cyclopropanecarboxylic acid 
• 530-48-3 1,1-Diphenylethylene 
• 5350-57-2 benzophenone hydrazone 
• 67428-04-0 ethyl 2,2-diphenylcyclopropane-1-carboxylate 
• 28098-84-2 1-cyano-2,2-diphenylcyclopropane 
• 107-02-8 acrolein 
• 908093-98-1 diazodiphenylmethane 
• 19179-60-3 methyl 2,2-diphenylcyclopropane-1-carboxylate 
• 119-61-9 benzophenone 

Downstream Products

• 84313-28-0 (Z)-1-(2,2-Diphenylcyclopropyl)-3-phenyl-1,3-butadien 
• 95188-05-9 N-(2,2-diphenylcyclopropyl)methylideneaniline 
• 214824-91-6 (E)-N-methoxy-N-methyl-3-(2,2-diphenylcyclopropyl)propenamide 
• 228860-00-2 5-(2,2-diphenylcyclopropyl)-4-pentenoic acid 
• 808756-14-1 2,4-dimethoxybenzyl 3-hydroxy-3-(2,2-diphenylcyclopropyl)-2,2-dimethylpropanoate 
• 808756-15-2 2,4-dimethoxybenzyl 3-(diphenylphosphatoxy)-3-(2,2-diphenylcyclopropyl)-2,2-dimethylpropanoate 
• 679417-90-4 3-(2,2-diphenyl-cyclopropyl)-3-hydroxy-2-methoxy-2-methyl-propionic acid ethyl ester 
• 413615-58-4 (2,2-diphenylcyclopropyl)acetaldehyde 
• 119981-84-9 ethyl (E)-3-(2,2-diphenylcyclopropyl)acrylate 
• 934009-26-4 [2-(2,2-dibromovinyl)-1-phenylcyclopropyl]benzene 
• 936140-30-6 (E)-3-(2,2-diphenylcyclopropyl)prop-2-en-1-ol 

Relevant academic research and scientific papers

Reactivity of cyclopropanic δ-oxo-α,β-unsaturated esters towards SmI2: 3-exo-trig cyclisation versus cyclopropane ring opening

trans-(2′,2′-Diphenyl-bicyclopropyl-2-yl)-4,4-dimethyl-5-oxo-pent-2-enoic acid methyl ester 9, undergoes 3-exo-trig cyclisation in the presence of SmI2 without competitive ring opening of Newcomb's bicyclopropylic probe next to the carbonyl gro

Direct and Stereospecific [3+2] Synthesis of Pyrrolidines from Simple Unactivated Alkenes

Pyrrolidines are important heterocyclic compounds with endless applications in organic synthesis, metal catalysis, and organocatalysis. Their potential as ligands for first-row transition-metal catalysts inspired a new method to access complex poly-heterocyclic pyrrolidines in one step from available materials. This fundamental step forward is based on the discovery of an essential organoaluminum promoter that engages unactivated and electron-rich olefins in intermolecular [3+2] cycloadditions.

Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes

Addition of allylmagnesium reagents to an aliphatic aldehyde bearing a radical clock gave only addition products and no evidence of ring-opened products that would suggest single-electron-transfer reactions. The analogous Barbier reaction also did not pro

Diazo- And transition-metal-free C-H insertion: A direct synthesis of β-lactams

Carbene intermediates are very useful species for a range of reactions including C-H insertions and cycloadditions. They are most commonly generated by metal-catalyzed release of nitrogen gas from diazo precursors. Herein, we present a novel C-H insertion

Aryl-substituted cyclopropyl acetylenes as sensitive mechanistic probes in the gold-catalyzed hydration of alkynes. comparison to the Ag(I)-, Hg(II)-, and Fe(III)-catalyzed processes

The gold-catalyzed hydration of 2-phenyl- or 2,2-diphenylcyclopropyl acetylene, sensitive probes to trace the formation of vinyl carbocations, provides exclusively the corresponding cyclopropyl methyl ketones. On the other hand, in the Ag(I)- or Fe(III)-c

Cyclopropanes in Nicholas reaction: Formation of spiroketals with a five-membered and a seven- or an eight-membered ring This paper is dedicated to Professor Paul A. Wender, one of the most creative contributors to the broad discipline of organic chemistry, on the occasion of the Tetrahedron Prize

The consecutive treatment of 5-hydroxy-1-pentynyl 2,2-disubstituted- cyclopropyl ketones with Co2(CO)8 and BF 3·OEt2 produced the corresponding Co 2(CO)6-complexed dioxaspiro[4.6] derivatives. The one-carbon homologated substrates also afforded dioxaspiro[4.7]. It was found that this procedure can be applied to the substrates with gem-disubstituents as well as a mono-aryl substituent on the cyclopropane, but the mono-alkyl substituted cyclopropanes are insufficient.

1-[(E)-2-arylethenyl]-2,2-diphenylcyclopropanes: Kinetics and mechanism of rearrangement to cyclopentenes

Kinetic measurements for the thermal rearrangement of 2,2-diphenyl-1-[(E)- styryl]cyclopropane (22a) to 3,4,4-triphenylcyclopent-1-ene (23a) in decalin furnished ΔHρm{{-{isom}^{ne }}}$=31.0±1.2kcal mol-1 and ΔSρm{{-{isom}^{ne }}}$=-6. 0±2.6e.u. The lowering of ΔHa‰ by 20kcal mol-1, compared with the rearrangement of the vinylcyclopropane parent, is ascribed to the stabilization of a transition structure (TS) with allylic diradical character. The racemization of (+)-(S)-22a proceeds with ΔHρm{{-{rac}^{ne }}}$=28.2±0.8kcal mol -1 and ΔSρm{{-{rac}^{ne }}}$=-5±2e.u., and is at 150° 106 times faster than the rearrangement. Seven further 1-(2-arylethenyl)-2,2-diphenylcyclopropanes 22, (E)- and (Z)-isomers, were synthesized and characterized. The (E)-compounds showed only modest substituent influence in their krac (at 119.4°) and kisom (at 159.3°) values. The lack of solvent dependence of rate opposes charge separation in the TS, but a linear relation of log krac with log p.r.f., i.e., partial rate factors of radical phenylations of ArH, agrees with a diradical TS. The ring-opening of the preponderant s-trans-conformation of 22 gives rise to the 1-exo-phenylallyl radical 26 that bears the diphenylethyl radical in 3-exo-position, and is responsible for racemization. The 1-exo-3-endo-substituted allylic diradical 27 arises from the minor s-gauche-conformation of 22 and is capable of closing the three- or the five-membered ring, 22 or 23, respectively. The discussion centers on the question whether the allylic diradical is an intermediate or merely a TS. Quantum-chemical calculations by Houk etal. (1997) for the parent vinylcyclopropane reveal the lack of an intermediate. Can the conjugation of the allylic diradical with three Ph groups carve the well of an intermediate? Copyright

SmI2-mediated reductive cross-coupling reactions of -cyclopropyl nitrones

Three new α-cyclopropyl nitrones have been synthesized as mechanistic probes for reductive cross-coupling reactions of nitrones. The α-cyclopropylcarbinyl radical intermediate formed by single electron transfer from SmI2 to these nitrones is no

Concerning the reactivity of ptad with isomeric dienes: The mechanism of the Diels-Alder cycloaddition

Cyclopropyl substituted dienes are employed as mechanistic probes in the triazolinedione Diels-Alder (DA) reaction. In aprotic and protic solvents, apart from the DA adducts that bear an intact cyclopropyl group, complicated and rearranged products are also obtained. These results provide solid evidence for the involvement of an open intermediate with a lifetime greater than 2 x 10 -12 s.

Facile and efficient way to synthesize the radical cyclization precursor methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3-oxo-2- (phenylseleno)propanoate for kinetic research

Methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3- oxo-2-(phenylseleno)propanoate was prepared in 10 steps in good to excellent yield using benzophenone and hydrazine hydrate as the starting materials. Copyright Taylor & Francis Group, LLC.