The orientation of substitution in metallation of dimethylaminomethyl-, hydroxymethyl- and diphenylphospino-cymantrenes

Loim, N. M.; Kondrat'ev, P.V.; Соловьева, Н. П.; Antonovich, V. A.; Petrovskii, P. V.; Парнес, З. Н.; Kursanov, D. N.

doi:10.1016/s0022-328x(00)93594-0

Cited by 23 publications

(5 citation statements)

References 3 publications

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“…8 was prepared according to a procedure similar to that for compound 1 from hydroxymethylcymanrene (5.2 g, 22.2 mmol), NaH (60% suspension, 1.6 g, 40 mmol), and allyl bromide (2.9 mL, 33.3 mmol). The yield was 4.3 g (72%).…”

Section: Methodsmentioning

confidence: 99%

Photochemistry of π- and n-Donor Bifunctional Monosubstituted Derivatives of Cyclopentadienylmanganese Tricarbonyl Complexes Containing an Allyl Group and Photo- and Thermoisomerization of the Corresponding Dicarbonyl Chelates

et al. 2011

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Photochemical properties of a series of bifunctional monosubstituted derivatives of cymantrene containing a C-, N-, or O-bound π-allyl group, along with n-donating carbamate, amide, or pyridine fragments were investigated. The results obtained demonstrate that the nature and thermodynamic stability of the cyclopentadienylmanganese dicarbonyl chelates derived from bifunctional monosubstituted cymantrene derivatives depend substantially on both the nature of the functional groups and on their position in the substituent at the Cp ring. Thus, for the six-membered chelates, the thermodynamic stability increases in the series carbamates < amides < pyridines < olefins. Some of the dicarbonyl chelates studied form reversible photochromic systems due to linkage isomerization between different donating groups of the bifunctional substituent and the manganese atom with a wide range of times of thermal isomerization.

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Section: Methodsmentioning

confidence: 99%

Photochemistry of π- and n-Donor Bifunctional Monosubstituted Derivatives of Cyclopentadienylmanganese Tricarbonyl Complexes Containing an Allyl Group and Photo- and Thermoisomerization of the Corresponding Dicarbonyl Chelates

et al. 2011

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“…To a solution of cymantrenylmethanol [33] (4 g, 17 mmol) in dry benzene (40 mL) was added PBr 3 (0.8 mL, 8.5 mmol) at 15°C, and the temperature of the reaction mixture increased to 25°C. The reaction mixture was kept at this temperature for 3 h, cooled to 10°C, and then poured into cool water.…”

Section: Synthesis Of Cymantrenylmethyl Bromidementioning

confidence: 99%

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

et al. 2016

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The synthesis of four new 1,2,3‐triazole derivatives and seven 1,2,3‐triazolium salts that contain an organometallic group (i.e., cymantrenyl and ferrocenyl) at either the N‐1, N‐2, or N‐3 position was realized. The alkylation of organometallic and organic triazole derivatives was investigated, and as a result of these studies, it was found that the presence of a good leaving group at the heterocyclic nitrogen atom led to transalkylation and subsequent migration of the N‐1 substituent to the N‐2 position of the triazole moiety. The nucleophilicity of the counterion of the triazolium salt influenced the transalkylation and isomerization processes, which suggests that the elimination of the N‐substituent most likely occurs though a concerted mechanism with nucleophilic assistance from the counterion. Thus, a new approach to the synthesis of 2,4‐disubstituted 1,2,3‐triazoles has been developed.

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“…The spirodiene 98 so produced was identical in all respects to that produced starting from the brucine-resolved diacid 96. Thermolysis of the spirodiene as before gave (S)-(-)-91, which was confirmed to be enantiomerically pure by using the previous method of chiral shift spectroscopy. This four-step synthesis described produced (S)-(-)-91 in about 30% overall yield from commercially available l-bromo-2-methylnaphthalene (92). The chiral phosphine needed for the asymmetric catalytic coupling reaction is available as either enantiomer, enabling a facile, large-scale synthesis of both enantiomers of the chiral cyclopentadiene ligand (S)-91 or (fl)-91.…”

Section: Cz-symmetrlcal Annulated Cyclopentadienesmentioning

confidence: 99%

Synthesis and applications of chiral cyclopentadienylmetal complexes

Halterman¹

1992

Chem. Rev.

561

227

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The orientation of substitution in metallation of dimethylaminomethyl-, hydroxymethyl- and diphenylphospino-cymantrenes

Cited by 23 publications

References 3 publications

Photochemistry of π- and n-Donor Bifunctional Monosubstituted Derivatives of Cyclopentadienylmanganese Tricarbonyl Complexes Containing an Allyl Group and Photo- and Thermoisomerization of the Corresponding Dicarbonyl Chelates

Photochemistry of π- and n-Donor Bifunctional Monosubstituted Derivatives of Cyclopentadienylmanganese Tricarbonyl Complexes Containing an Allyl Group and Photo- and Thermoisomerization of the Corresponding Dicarbonyl Chelates

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

Synthesis and applications of chiral cyclopentadienylmetal complexes

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