15677-15-3

Usage

InChI:InChI=1/C10H10/c1-2-4-9-7(3-1)5-8-6-10(8)9/h1-4,8,10H,5-6H2

Upstream product

• 73774-57-9 trans-N-<(2-Allylphenyl)methylene>-2,3-diphenyl-1-aziridinamine 
• 56485-66-6 1,1-dichloro-1,1a,6,6a-tetrahydrocyclopropindene 
• 95-13-6 1-indene 
• 361444-94-2 iodomethyl perfluoropentanoate 
• 14399-53-2 bis(iodomethyl)zinc 
• 75-09-2 dichloromethane 
• 73774-56-8 2,3,4,5-Tetrahydro-3-<(4-methylphenyl)sulfonyl>-1,4-methano-1H-2,3-benzodiazepine 
• 91-14-5 1,2-divinylbenzene 
• 74-95-3 1,1-dibromomethane 
• 75-11-6 diiodomethane 
• 73774-59-1 4,5-Dihydro-1,4-methano-1H-2,3-benzodiazepine 
• 73774-58-0 3,3a,4,8b-Tetrahydroindeno<1,2-c>pyrazole 
• 73774-60-4 o-Allylbenzaldehyde Tosylhydrazone 
• 62708-42-3 o-allylbenzaldehyde 

Downstream Products

• 348080-87-5 2‐(bromomethyl)‐2,3‐dihydro‐1H‐indene 
• 767-59-9 1-Methylinden 
• 18933-48-7 1-Bromcycloprop<2,3>inden 
• 18926-25-5 1-bromomethyl-indene 
• 91-20-3 naphthalene 
• 447-53-0 1,2-Dihydronaphthalene 
• 91-14-5 1,2-divinylbenzene 
• 612-17-9 1,4-dihydronaphthalene 
• 68846-65-1 2-methylene-2,3-dihydro-1H-indene 
• 20710-24-1 3-methoxytetralin 
• 133055-26-2 2-Methoxymethylindan 

Relevant academic research and scientific papers

Preparation of a storable zinc carbenoid species and its application in cyclopropanation, chain extension, and [2,3]-sigmatropic rearrangement reactions

(Chemical Equation Presented) The formation of a new phosphate carbenoid (n-BuO)2P(O)OZnCH2I and its application in organozinc-mediated reactions is described. This carbenoid undergoes very slow degradation in solution and can be stored for several weeks at -20 °C. Its reactivity was tested with many representative alkenes and was determined to be a powerful cyclopropanating reagent, giving the corresponding cyclopropanes in 72-99% yield. The use of this carbenoid in the chain extension of 1,3-diketones and [2,3]-sigmatropic rearrangement reactions is also described. 2010 American Chemical Society.

Acetyl Chloride Promoted Cyclopropanations of Alkenes with Dibromomethane Using Zinc Dust and Copper(I) Chloride in Ether

Acetyl chloride strongly accelerates the cyclopranation reactions of alkenes with dibromomethane or diiodomethane using zinc dust and copper(I) chloride in ether and results in improved yields of cyclopropane products.

Rhodium(II)- or Copper(I)-Catalyzed Formal Intramolecular Carbene Insertion into Vinylic C(sp2)?H Bonds: Access to Substituted 1H-Indenes

A rhodium(II)- or copper(I)-catalyzed formal intramolecular carbene insertion into vinylic C(sp2)?H bonds is reported herein. This method provides straightforward access to 1H-indenes with high efficiency and excellent functional-group compatibility. Mechanistically, the reaction is proposed to involve the following sequence: metal carbene formation, intramolecular nucleophilic addition of the double bond to the electron-deficient carbene carbon atom, dearomatization, and finally a 1,5-H shift.

Aminofluorination of Cyclopropanes: A Multifold Approach through a Common, Catalytically Generated Intermediate

We have discovered a highly regioselective aminofluorination of cyclopropanes. Remarkably, four unique sets of conditions-two photochemical, two purely chemical-generated the same aminofluorinated adducts in good to excellent yields. The multiple, diverse ways in which the reaction could be initiated provided valuable clues that led to the proposal of a "unifying" chain propagation mechanism beyond initiation, tied by a common intermediate. In all, the proposed mechanism herein is substantiated by product distribution studies, kinetic analyses, LFERs, Rehm-Weller estimations of ΔGET, competition experiments, KIEs, fluorescence data, and DFT calculations. From a more physical standpoint, transient-absorption experiments have allowed direct spectroscopic observation of radical ion intermediates (previously only postulated or probed indirectly in photochemical fluorination systems) and, consequently, have provided kinetic support for chain propagation. Lastly, calculations suggest that solvent may play an important role in the cyclopropane ring-opening step.

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Dinuclear Ni complexes supported by naphthyridine-diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional-group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively low cyclopropane yields (≤20 %). These results constitute an entry into catalytic carbene transformations from oxidized methylene precursors.

Synergistic effect of additives on cyclopropanation of olefins

An efficient cyclopropanation of olefins with Zn(CH2I) 2, a catalytic amount of CCl3CO2H, and 1,2-dimethoxyethane at room temperature is described. A wide variety of olefins, including acid-sensitive substrates,

Cyclopropanation of alkenes with CH2I2/Et3Al by the phase-vanishing method based on fluorous phase screen

Phase-vanishing (PV) method using perfluorohexanes as a screen phase was applied to cyclopropanation reactions with CH2I2/Et2Zn and CH2I2/Et3Al. When Et3Al was used as a carbenoid generator, the reaction proceeded smoothly and desired cyclopropane derivatives were obtained in high yield. The PV cyclopropanation took 2 or 3 days to complete, however, reduction of reaction time by a factor of 2-3 was also achieved by vigorous stirring after the bottom CH2I2 layer disappeared.

A Novel Class of Tunable Zinc Reagents (RXZnCH2Y) for Efficient Cyclopropanation of Olefins

A class of zinc reagents (RXZnCH2Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.

Photoinduced reduction of gem-dichlorocyclopropanes with SmI2 and benzenethiol

Upon irradiation with visible light, gem-dichlorocyclopropanes undergo reductive dechlorination with samarium diiodide and benzenethiol to provide the corresponding cyclopropanes in good yields. The reaction may proceed via the hydrogen abstraction from PhSH by cyclopropyl radicals formed in situ by the reduction with SmI2.

Synthesis of paddlanes possessing cyclophane shaft and cyclobutane blades

1,2- And 1,2,4,5-paddlanes were successfully prepared by the intermolecular [2 + 2] photocycloaddition of o-divinyl- and 1,2,4,5-tetravinylbenzenes, respectively. On the other hand, no desired paddlanes were obtained from p-divinyl- or 1,2,3-trivinylbenze