Paul M. Treichel, in Comprehensive Organometallic Chemistry II, 1995. 2.66) (04RJG105). They are used to prepare cyclopentadienyl complexes. However, 69 takes a structure with localized charge (70) in a polar solvent, regarded as a nonaromatic compound. Cyclopentadiene is an organic compound with the formula C 5 H 6.This colorless liquid has a strong and unpleasant odor.At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a Diels–Alder reaction.This dimer can be restored by heating to give the monomer.. The observed slow exchange of metal-bound hydrogen with the cyclopentadienyl hydrogen atoms then requires the movement of an exo hydrogen atom, possibly by an intramolecular sigmatropic shift around the η4-cyclopentadiene ring.474, An intermolecular transfer of benzyl to η5-C5H5 is suggested for reaction (96) since the benzyl group is introduced exo to iron.208 In almost all other cases, the reaction products are substitution products even though addition products are intermediates. Other reactions of cyclopentadienyl derivatives include the attack of Cp on intermediate trimethylenemethane species discussed above (Section 8.06.6.3), and the reductive elimination of Pd(η5-Cp)(η3-allyl) to give Pd metal by CVD techniques (Section 8.06.6.2.4). Famously, cyclopentadiene dimerizes. The insertion of an alkyne into Pd–C bonds of vinyl substituted aryls, followed by intramolecular alkene insertion, also leads to highly substituted indenyl palladium complexes. Cocondensation of chromium or molybdenum vapors gives η6-sandwiches (Eq. The organosamarium catalyst and cyclohydroamination approach was used for the synthesis of naturally occurring alkaloids, such as pyrrolidine 197B [(2S, 5S,)-trans-2-butyl-5-pentylpyrrolidine].263 The catalytic ring-closure produced the desired trans-pyrrolidine, with a pendant olefin with excellect Z selectivity (Scheme 155). To obtain cyclopentadiene monomer, commercial dicyclopentadiene is cracked by heating to ~ 180 °C. Chem.
At room temperature, this cyclic diene dimerizes over the course of hours to give dicyclopentadiene via a DielsâAlder reaction. Scheme 155. The catalytic cycle for this reaction is presented in (Scheme 154). Deprotonation can be achieved with a variety of bases, typically sodium hydride, sodium metal, and butyl lithium.
2Cp-H + 2KOH + FeCl 2 à (η 5-Cp) 2 Fe + H 2 O + 2KCl (1) This can be done with a variety of bases.
Cyclopentadiene is an organic compound with the formula C5H6. per equiv. Chem. Salts of this anion are commercially available, including sodium cyclopentadienide and lithium cyclopentadienide. The results of NMR measurement in addition to the features above indicated their nonaromatic character. Next, 4.0mL of Ethyl acetate and 4.0mL of Ligroin (Petroleum ether) were separately poured into the same flask. The η6-coordinated benzothiophene and dibenzothiophene iridium(III) are made as shown in Eq. Cyclopentadiene production is usually not distinguished from dicyclopentadiene since they are interconverted. 2.65) (11JOM2451). comprises reacting a Grignard reagent with the deriv. The average FeC distance (2.070 Å) is only slightly longer than in ferrocene. It was synthesized by reaction of Tl(Cp-PPh2) with PdClMe(COD).692, An interesting heterometallic Pd–Ta derivative was prepared, as shown in Scheme 84.
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