Substituent effects on the relative rates and free energies of ortho-lithiation reactions: families of fluorobenzenes as the substrates

Autor: Elena Marzi, Frédéric R. Leroux, Manfred Schlosser, Christophe Curty, Florence Mongin

Publikováno v: ARKIVOC-Online Journal of Organic Chemistry
ARKIVOC-Online Journal of Organic Chemistry, Arkat USA Inc, 2015, 4, pp.48-65. ⟨10.3998/ark.5550190.p008.926⟩
ARKIVOC, Vol 2015, Iss 4, Pp 48-65 (2015)

2-, 3- and 4-substituted fluorobenzenes and 5-substituted 1,3-difluorobenzenes were metalated with sec-butyllithium (LIS) and with lithium 2,2,6,6-tetramethylpiperidide (LiTMP) under irreversible conditions in order to determine the rates of reaction

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ad5f75e52905ec0a07320076a10cc4bf
https://hal.archives-ouvertes.fr/hal-02304104

Metalation and Derivatization of All Six Dichlorobenzotrifluorides:Site Selectivities

Autor: Manfred Schlosser, Eric Masson, Elena Marzi, Carla Bobbio, Fabrice Cottet

Publikováno v: European Journal of Organic Chemistry. 2005:4393-4400

The metalation of 2,3-, 2,6-, 2,4- and 3,5-dichlorobenzotrifluorides can be readily effected with std. reagents such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, and butyllithium at the chlorine-adjacent 4- and 3-positions and

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::93c5662d0f56fa88680b132a6f2b45b6
https://doi.org/10.1002/ejoc.200500240

The site-selective functionalization of halogen-bearing phenols: an exercise in diversity-oriented organometallic synthesis

Autor: Elena Marzi, Manfred Schlosser

Publikováno v: Tetrahedron. 61:3393-3401

The organometallic approach to diversity-oriented org. synthesis was subjected to a further test, this time in the phenol series. The model compds. selected were 2,3,6-trifluorophenol, the three isomers of (trifluoromethoxy)phenol and the three isome

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::58cab5aa1ba3d14f5ffdbb9de403cd7f
https://doi.org/10.1016/j.tet.2004.10.103

Enhancement of Benzylic Basicity by a Fluorine Substituent at thepara-Position: A Case of Lone Pair/Lone Pair Repulsion

Autor: Ferenc Faigl, Manfred Schlosser, Elena Marzi

Publikováno v: Chemistry - A European Journal. 6:771-777

The introduction of a halogen atom at any arom. position of toluene considerably accelerates the base-promoted deprotonation of the Me group. P-Fluorotoluene is the only exception; proton abstraction from its benzylic site occurs approx. at one tenth

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::6dc6aa4afa1d94873d5c907f4f3a9f3b
https://doi.org/10.1002/(sici)1521-3765(20000303)6:5<771::aid-chem771>3.0.co

Calixarenes with exo-hydroxy groups: Synthesis, crystal and molecular structure of ortho-tert-butylphenol-based calix[4]-, calix[6]- and calix[8]arenes

Autor: Elena Marzi, Maurizio Lanfranchi, Franca Bigi, Cecilia Porta, Giovanni Sartori, Raimondo Maggi, Francesco Peri, Maria Angela Pellinghelli

Publikováno v: Tetrahedron. 53:3287-3300

Ortho-tert-butylcalixarenes 3, 4 and 5 with exo-hydroxy groups were synthesised by tin tetrachloride-promoted condensation of 2,2′-dihydroxy-3,3′-di-tert-butyldiphenylmethane 6 with formaldehyde. While 1H NMR analysis of compounds 3, 4 and 5 reve

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::b168810f4bd14fc398e8fd2a64b61562
https://doi.org/10.1016/s0040-4020(97)00039-2