scholarly journals Fluorinated photoremovable protecting groups: the influence of fluoro substituents on the photo-Favorskii rearrangement

2008 ◽  
Vol 7 (5) ◽  
pp. 614 ◽  
Author(s):  
Kenneth F. Stensrud ◽  
Dominik Heger ◽  
Peter Šebej ◽  
Jakob Wirz ◽  
Richard S. Givens
Keyword(s):  
Protecting Groups ◽  
Favorskii Rearrangement ◽  
Photoremovable Protecting Groups

scholarly journals p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

2011 ◽  
Vol 89 (3) ◽  
pp. 364-384 ◽  
Author(s):  
Richard S. Givens ◽  
Kenneth Stensrud ◽  
Peter G. Conrad ◽  
Abraham L. Yousef ◽  
Chamani Perera ◽  
...  
Keyword(s):  
Aqueous Media ◽  
Protecting Groups ◽  
Quantum Yields ◽  
Photochemical Rearrangement ◽  
Favorskii Rearrangement ◽  
Leaving Group ◽  
Predominant Form ◽  
Photoremovable Protecting Groups ◽  
Conjugate Base ◽  
Modest Effect

A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO2R, CONH2, and CH3 have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pKa of the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.

scholarly journals Competing pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation

2020 ◽  
Vol 19 (10) ◽  
pp. 1364-1372
Author(s):  
Thomas Field ◽  
Julie Peterson ◽  
Chicheng Ma ◽  
Pradeepkumar Jagadesan ◽  
José P. Da Silva ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Protecting Groups ◽  
Photoremovable Protecting Groups ◽  
Competing Pathways

Photolysis of p-hydroxyphenacyloxy arenes releases free phenols in good yields governed by their pKa. At high pKa, new byproducts (Bvs. A) reveal a change in reaction mechanism.

scholarly journals A general strategy for visible-light decaging based on the quinone cis-alkenyl lock

2019 ◽  
Vol 55 (34) ◽  
pp. 4965-4968 ◽  
Author(s):  
David P. Walton ◽  
Dennis A. Dougherty
Keyword(s):  
Visible Light ◽  
Protecting Groups ◽  
General Strategy ◽  
Thermal Cyclization ◽  
Coumaric Acid ◽  
Photoremovable Protecting Groups

Combining the fast thermal cyclization of o-coumaric acid derivatives with the intramolecular photoreduction of quinones gives new visible-light photoremovable protecting groups absorbing well above 450 nm.

scholarly journals Synthesis of Caged Nucleosides with Photoremovable Protecting Groups Linked to Intramolecular Antennae

2005 ◽  
Vol 88 (4) ◽  
pp. 891-904 ◽  
Author(s):  
Joulia Smirnova ◽  
Dominik Wöll ◽  
Wolfgang Pfleiderer ◽  
Ulrich E. Steiner
Keyword(s):  
Protecting Groups ◽  
Photoremovable Protecting Groups

Molecular Engineering of Photoremovable Protecting Groups for Two-Photon Uncaging

2008 ◽  
Vol 120 (49) ◽  
pp. 9667-9671 ◽  
Author(s):  
Sylvestre Gug ◽  
Frédéric Bolze ◽  
Alexandre Specht ◽  
Cyril Bourgogne ◽  
Maurice Goeldner ◽  
...  
Keyword(s):  
Molecular Engineering ◽  
Protecting Groups ◽  
Two Photon ◽  
Photoremovable Protecting Groups

Photoremovable Protecting Groups

ChemInform ◽  
2004 ◽  
Vol 35 (15) ◽  
Author(s):  
Richard S. Givens ◽  
II Conrad, Peter G. ◽  
Abraham L. Yousef ◽  
Jong-Ill Lee
Keyword(s):  
Protecting Groups ◽  
Photoremovable Protecting Groups
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