Verbesserte Herstellung von<i>t</i>-Butoxycarbonyl-fluorid und dessen Verwendung zur Synthese von 1-Boc-3-for-mylindol, einem neuen Reagenz zur Verknüpfung von Peptid-Fragmenten

Wackerle, Lorenz; Ugi, lvar

doi:10.1055/s-1975-23848

Cited by 20 publications

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“…Commercially available phosgene (Matheson), F 2 CO (PCR Research Chemicals), AsF 5 , and SbF 5 (Ozark Mahoning) were purified by fractional condensation prior to use. Literature methods were used for the syntheses of ClFCO, Cl 2 CO·SbF 5 , and tert -butyl fluoroformate …”

Section: Methodsmentioning

confidence: 99%

“…Literature methods were used for the syntheses of ClFCO, 13 Cl2CO‚ SbF5, 14 and tert-butyl fluoroformate. 15 Volatile materials were handled in a stainless steel vacuum line equipped with Teflon-FEP U-traps, stainless steel bellows-seal valves, and a Heise Bourdon tube-type pressure gauge. 16 The line and other hardware were passivated with ClF3 and HF.…”

Section: Methodsmentioning

confidence: 99%

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Existence of the Halocarbonyl and Trifluoromethyl Cations in the Condensed Phase

et al. 1999

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Experimental and theoretical studies show that neither CF3 + nor FCO+ can be stabilized in the condensed phase with presently known Lewis acids. In the case of ClCO+, stabilization with SbF6 - was also not possible, but Sb3F15 possesses sufficient acidity to abstract a fluoride ion from ClFCO in the formation of ClCO+Sb3F16 -. This salt was fully characterized, providing the first well-established proof for the existence of a halocarbonyl cation in the condensed phase. Theoretical calculations and thermochemical cycles were used to corroborate our experimental findings, demonstrating that is possible to predict correctly whether a molecule with three different donor sites, such as ClFCO, will form an oxygen-coordinated donor−acceptor adduct or undergo either F- or Cl- abstraction. Furthermore, a method is described for extending natural bond orbital (NBO) analyses to systems containing two different types of competing, p(π) back-donating ligands.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Existence of the Halocarbonyl and Trifluoromethyl Cations in the Condensed Phase

et al. 1999

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tert‐Butoxycarbonyl‐L‐Proline

et al. 2003

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tert ‐Butoxycarbonyl‐ L ‐proline reactant: 115 g. (1.00 mole) of 1,1,3,3‐tetramethylguanidine product: tert ‐butoxycarbonyl‐ L ‐proline product: Boc‐Ala product: Boc‐Ala product: Boc‐Asn product: Boc‐Asp product: Boc‐Cys(Bzl) product: Boc‐Cys (Bzl) product: Boc‐Gln product: Boc‐Glu product: Boc‐Ile product: Boc‐Leu product: Boc‐Met product: Boc‐Phe product: Boc‐Phe product: Boc‐Phe product: Boc‐Phe product: Boc‐Phe product: Boc‐Pro product: Boc‐Pro product: Boc‐Pro product: Boc‐Thr product: Boc‐Val

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Indole Aldehydes and Ketones

Remers¹

1979

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Verbesserte Herstellung vont-Butoxycarbonyl-fluorid und dessen Verwendung zur Synthese von 1-Boc-3-for-mylindol, einem neuen Reagenz zur Verknüpfung von Peptid-Fragmenten

Cited by 20 publications

References 0 publications

Existence of the Halocarbonyl and Trifluoromethyl Cations in the Condensed Phase

Existence of the Halocarbonyl and Trifluoromethyl Cations in the Condensed Phase

tert‐Butoxycarbonyl‐L‐Proline

Indole Aldehydes and Ketones

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