Matches in SemOpenAlex for { <https://semopenalex.org/work/W2012372257> ?p ?o ?g. }
- W2012372257 endingPage "7995" @default.
- W2012372257 startingPage "7988" @default.
- W2012372257 abstract "The hydrolysis rates of a series of protected p-hydroxybenzyl halides designed to generate a p-quinone methide through 1,6-elimination following photolytic deprotection have been investigated in order to optimize hydrolytic stability. A number of p-hydroxybenzyl halides containing an ether- or carbonate-linked photolabile hydroxy protecting group and a fluoride, chloride, or bromide benzylic leaving group have been synthesized. The hydrolysis rates of these derivatives in different water/acetonitrile mixtures and temperatures have been determined. The hydrolysis half-life of the benzyl bromide with the p-hydroxy protected as the carbonate-linked α-methylnitroveratryl (18c) is more than 750 times that of the ether-linked analogue (16c). These studies afford a Hammett σp+ of +0.28 for the carbonate-linked derivatives compared to a σp+ of −0.39 for the ether-linked derivatives. The theoretical hydrolysis half-life of the most stable benzyl fluoride in 100% water was sufficiently long so as to preclude extrapolation, while the chloride was approximately 50 h, and even the bromide was estimated to be nearly 5 h." @default.
- W2012372257 created "2016-06-24" @default.
- W2012372257 creator A5044094298 @default.
- W2012372257 creator A5048882303 @default.
- W2012372257 date "1999-09-30" @default.
- W2012372257 modified "2023-09-23" @default.
- W2012372257 title "Hydrolytic Stabilization of Protected <i>p</i>-Hydroxybenzyl Halides Designed as Latent Quinone Methide Precursors" @default.
- W2012372257 cites W1498196254 @default.
- W2012372257 cites W1963651070 @default.
- W2012372257 cites W1966212444 @default.
- W2012372257 cites W1966814641 @default.
- W2012372257 cites W1968685749 @default.
- W2012372257 cites W1979758767 @default.
- W2012372257 cites W1983346025 @default.
- W2012372257 cites W1988000017 @default.
- W2012372257 cites W1989625861 @default.
- W2012372257 cites W1993891539 @default.
- W2012372257 cites W2001285013 @default.
- W2012372257 cites W2011331714 @default.
- W2012372257 cites W2012777392 @default.
- W2012372257 cites W2024229295 @default.
- W2012372257 cites W2027684924 @default.
- W2012372257 cites W2027721751 @default.
- W2012372257 cites W2029365955 @default.
- W2012372257 cites W2029939153 @default.
- W2012372257 cites W2032785646 @default.
- W2012372257 cites W2036465491 @default.
- W2012372257 cites W2039872051 @default.
- W2012372257 cites W2041341167 @default.
- W2012372257 cites W2041930769 @default.
- W2012372257 cites W2051439271 @default.
- W2012372257 cites W2053066252 @default.
- W2012372257 cites W2055240213 @default.
- W2012372257 cites W2055631666 @default.
- W2012372257 cites W2061451400 @default.
- W2012372257 cites W2061588119 @default.
- W2012372257 cites W2064660225 @default.
- W2012372257 cites W2069439618 @default.
- W2012372257 cites W2070049831 @default.
- W2012372257 cites W2070060989 @default.
- W2012372257 cites W2071451059 @default.
- W2012372257 cites W2072982389 @default.
- W2012372257 cites W2074705487 @default.
- W2012372257 cites W2077034602 @default.
- W2012372257 cites W2079041638 @default.
- W2012372257 cites W2086571661 @default.
- W2012372257 cites W2093468577 @default.
- W2012372257 cites W2094068577 @default.
- W2012372257 cites W2095305988 @default.
- W2012372257 cites W2106498256 @default.
- W2012372257 cites W2136573429 @default.
- W2012372257 cites W2139243647 @default.
- W2012372257 cites W2160701684 @default.
- W2012372257 cites W2160790360 @default.
- W2012372257 cites W2323189773 @default.
- W2012372257 cites W2324289681 @default.
- W2012372257 cites W2327012774 @default.
- W2012372257 cites W2335217515 @default.
- W2012372257 cites W2486148553 @default.
- W2012372257 cites W2950061470 @default.
- W2012372257 cites W2950648691 @default.
- W2012372257 cites W2950959614 @default.
- W2012372257 cites W2951748577 @default.
- W2012372257 cites W2951810408 @default.
- W2012372257 cites W4230191894 @default.
- W2012372257 cites W2022242888 @default.
- W2012372257 doi "https://doi.org/10.1021/jo991085t" @default.
- W2012372257 hasPublicationYear "1999" @default.
- W2012372257 type Work @default.
- W2012372257 sameAs 2012372257 @default.
- W2012372257 citedByCount "15" @default.
- W2012372257 countsByYear W20123722572012 @default.
- W2012372257 countsByYear W20123722572013 @default.
- W2012372257 countsByYear W20123722572014 @default.
- W2012372257 countsByYear W20123722572015 @default.
- W2012372257 countsByYear W20123722572016 @default.
- W2012372257 countsByYear W20123722572020 @default.
- W2012372257 countsByYear W20123722572021 @default.
- W2012372257 countsByYear W20123722572022 @default.
- W2012372257 crossrefType "journal-article" @default.
- W2012372257 hasAuthorship W2012372257A5044094298 @default.
- W2012372257 hasAuthorship W2012372257A5048882303 @default.
- W2012372257 hasConcept C155647269 @default.
- W2012372257 hasConcept C160964918 @default.
- W2012372257 hasConcept C161790260 @default.
- W2012372257 hasConcept C171560689 @default.
- W2012372257 hasConcept C178790620 @default.
- W2012372257 hasConcept C179104552 @default.
- W2012372257 hasConcept C185592680 @default.
- W2012372257 hasConcept C2776300020 @default.
- W2012372257 hasConcept C2778695967 @default.
- W2012372257 hasConcept C2779039209 @default.
- W2012372257 hasConcept C2780407432 @default.
- W2012372257 hasConcept C2780828025 @default.
- W2012372257 hasConcept C517835270 @default.
- W2012372257 hasConcept C94412978 @default.
- W2012372257 hasConceptScore W2012372257C155647269 @default.
- W2012372257 hasConceptScore W2012372257C160964918 @default.