Literature DB >> 18290649

The photo-Favorskii reaction of p-hydroxyphenacyl compounds is initiated by water-assisted, adiabatic extrusion of a triplet biradical.

Richard S Givens1, Dominik Heger, Bruno Hellrung, Yavor Kamdzhilov, Marek Mac, Peter G Conrad, Elizabeth Cope, Jong I Lee, Julio F Mata-Segreda, Richard L Schowen, Jakob Wirz.   

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Year:  2008        PMID： 18290649      PMCID： PMC3739295          DOI： 10.1021/ja7109579

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


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  14 in total

1.  Caged thiophosphotyrosine peptides.

Authors:  K Zou; W T Miller; R S Givens; H Bayley
Journal:  Angew Chem Int Ed Engl       Date:  2001       Impact factor: 15.336

2.  Catalytic subunit of protein kinase A caged at the activating phosphothreonine.

Authors:  Keyong Zou; Stephen Cheley; Richard S Givens; Hagan Bayley
Journal:  J Am Chem Soc       Date:  2002-07-17       Impact factor: 15.419

3.  Role of the retinal hydrogen bond network in rhodopsin Schiff base stability and hydrolysis.

Authors:  Jay M Janz; David L Farrens
Journal:  J Biol Chem       Date:  2004-10-08       Impact factor: 5.157

4.  Time-resolved resonance Raman and density functional theory study of hydrogen-bonding effects on the triplet state of p-methoxyacetophenone.

Authors:  Wing Sum Chan; Chensheng Ma; Wai Ming Kwok; David Lee Phillips
Journal:  J Phys Chem A       Date:  2005-04-21       Impact factor: 2.781

5.  Ultrafast time-resolved study of photophysical processes involved in the photodeprotection of p-hydroxyphenacyl caged phototrigger compounds.

Authors:  Chensheng Ma; Wai Ming Kwok; Wing Sum Chan; Peng Zuo; Jovi Tze Wai Kan; Patrick H Toy; David Lee Phillips
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

6.  Flash photolytic generation and study of p-quinone methide in aqueous solution. An estimate of rate and equilibrium constants for heterolysis of the carbon-bromine bond in p-hydroxybenzyl bromide.

Authors:  Y Chiang; A J Kresge; Y Zhu
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

7.  The mechanism of GTP hydrolysis by Ras probed by Fourier transform infrared spectroscopy.

Authors:  X Du; H Frei; S H Kim
Journal:  J Biol Chem       Date:  2000-03-24       Impact factor: 5.157

8.  A theoretical investigation of p-hydroxyphenacyl caged phototrigger compounds: an examination of the excited state photochemistry of p-hydroxyphenacyl acetate.

Authors:  Xuebo Chen; Chensheng Ma; Wai Ming Kwok; Xiangguo Guan; Yong Du; David Lee Phillips
Journal:  J Phys Chem A       Date:  2006-11-16       Impact factor: 2.781

9.  Ultrafast time-resolved transient absorption and resonance raman spectroscopy study of the photodeprotection and rearrangement reactions of p-hydroxyphenacyl caged phosphates.

Authors:  Chensheng Ma; Wai Ming Kwok; Wing Sum Chan; Yong Du; Jovi Tze Wai Kan; Patrick H Toy; David Lee Phillips
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

10.  New photoprotecting groups: desyl and p-hydroxyphenacyl phosphate and carboxylate esters.

Authors:  R S Givens; J F Weber; A H Jung; C H Park
Journal:  Methods Enzymol       Date:  1998       Impact factor: 1.600
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  14 in total

Review 1.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

2.  Simultaneous measurement and quantitation of 4-hydroxyphenylacetic acid and dopamine with fast-scan cyclic voltammetry.

Authors:  Mimi Shin; Sam V Kaplan; Kayla D Raider; Michael A Johnson
Journal:  Analyst       Date:  2015-03-18       Impact factor: 4.616

3.  Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.

Authors:  Roy Weinstain; Tomáš Slanina; Dnyaneshwar Kand; Petr Klán
Journal:  Chem Rev       Date:  2020-10-30       Impact factor: 60.622

4.  Stereochemically probing the photo-Favorskii rearrangement: a mechanistic investigation.

Authors:  Richard S Givens; Marina Rubina; Kenneth F Stensrud
Journal:  J Org Chem       Date:  2012-10-24       Impact factor: 4.354

Review 5.  Applications of p-hydroxyphenacyl (pHP) and coumarin-4-ylmethyl photoremovable protecting groups.

Authors:  Richard S Givens; Marina Rubina; Jakob Wirz
Journal:  Photochem Photobiol Sci       Date:  2012-02-16       Impact factor: 3.982

6.  The power of solvent in altering the course of photorearrangements.

Authors:  Peter Šebej; Bum Hee Lim; Bong Ser Park; Richard S Givens; Petr Klán
Journal:  Org Lett       Date:  2011-01-14       Impact factor: 6.005

7.  A photo-Favorskii ring contraction reaction: the effect of ring size.

Authors:  Viju Balachandran Kammath; Tomáš Šolomek; Bokolombe Pitchou Ngoy; Dominik Heger; Petr Klán; Marina Rubina; Richard S Givens
Journal:  J Org Chem       Date:  2012-06-19       Impact factor: 4.354

8.  p-Hydroxyphenacyl photoremovable protecting groups - Robust photochemistry despite substituent diversity.

Authors:  Richard S Givens; Kenneth Stensrud; Peter G Conrad; Abraham L Yousef; Chamani Perera; Sanjeewa N Senadheera; Dominik Heger; Jakob Wirz
Journal:  Can J Chem       Date:  2011-02-01       Impact factor: 1.118

9.  Competing pathways in the photo-Favorskii rearrangement and release of esters: studies on fluorinated p-hydroxyphenacyl-caged GABA and glutamate phototriggers.

Authors:  Kenneth Stensrud; Jihyun Noh; Karl Kandler; Jakob Wirz; Dominik Heger; Richard S Givens
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

10.  Fluorinated photoremovable protecting groups: the influence of fluoro substituents on the photo-Favorskii rearrangement.

Authors:  Kenneth F Stensrud; Dominik Heger; Peter Sebej; Jakob Wirz; Richard S Givens
Journal:  Photochem Photobiol Sci       Date:  2008-04-03       Impact factor: 3.982
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