A Stereospecific Cis Hydration of the Double Bond in Cyclic Derivatives

Brown, Herbert C.; Zweifel, George

doi:10.1021/ja01510a059

Cited by 113 publications

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“…One can postulate a pathway that involves radical anion formation, subsequent reaction with molecular oxygen, and then hydrogen abstraction. The last step is the same mechanism as the second step of the classical hydroboration–oxidation reaction 12…”

Section: Resultsmentioning

confidence: 99%

“…The last step is the same mechanism as the second step of the classical hydroboration-oxidation reaction. [12] Conclusion Overall, we have studied the gas-phase behaviors of arylboronic acids in detail under electrospray conditions. Mechanisms have been proposed for the formation of tetrahedral and trigonal species in aqueous and organic solutions, under neutral, acidic, and basic conditions.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

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Arylboronic Acid Chemistry under Electrospray Conditions

Wang

Dai

Burroughs

et al. 2013

Chemistry A European J

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Boronic acids are important in the organic and biological arenas. Thus, their identification and characterization are important. ESI-MS is a well-known tool for such uses. Herein we report a systematic analysis of the chemical behavior of arylboronic acids under ESI-MS conditions. Such information will be very critical to understanding the gas-phase chemistry of boronic acids in an ESI mass spectrometer ion source in general and the MS analysis of boronic acids and their macromolecular conjugates in particular.

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Section: Resultsmentioning

confidence: 99%

Section: Wwwchemeurjorgmentioning

confidence: 99%

Arylboronic Acid Chemistry under Electrospray Conditions

Wang

Dai

Burroughs

et al. 2013

Chemistry A European J

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“…240 Hydroboration-oxidation of compound 16 was achieved by treatment with BH3•THF followed by NaOH (aq) and H2O2 (Scheme 4). 243 The reaction gave a mixture of compounds 18 and 19 in a ratio of 9:1. This selectivity is interesting given that the two possible positions for the added alcohol functionality are both secondary carbons.…”

Section: Compoundmentioning

confidence: 99%

An insight into the metabolism of New Psychoactive Substances : Structural elucidation of urinary metabolites of synthetic cannabinoids and fentanyl analogues using synthesized reference standards

Wallgren

2020

Linköping Studies in Science and Technology. Dissertations

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New Psychoactive Substances (NPS) is an umbrella term covering hundreds of substances across different drug groups. Many of these substances were originally developed for therapeutic use but have later appeared on the recreational drug market. The use of NPS has been associated with many outbreaks leading to hospitalizations and has been implicated in numerous fatalities worldwide. To be able to analytically detect drugs in a forensic setting is vital in the fight against the abuse of NPS. One of the most notable challenges in detection of NPS is the identification of major urinary metabolites for use as biomarkers. Furthermore, given the lack of reference standards in most metabolism studies, the major urinary metabolites can often only be tentatively determined. Docent Johan Dahlén, my main supervisor, for allowing me the opportunity to carry out my research as a PhD student. Thank you for your positive attitude, support, encouragement and for your ability to turn problems into opportunities. Professor Peter Konradsson, my co-supervisor, for accepting me as a PhD student and for encouraging me to strive forward. Thank you for your guidance in chemistry as well as for your enjoyable music and sports analogies. Doctor Xiongyu Wu, my co-supervisor, for being an exceptional person and a master chemist. Thank you for always being there for me when I needed support or advice, never making me feel like a nuisance. You will always have my utmost admiration and appreciation. The people currently or previously working at the National Board of Forensic Medicine, Svante, Martin, Henrik, Anna, Robert, Ariane and Shimpei for excellent collaboration. Thank you for letting me partake in your fascinating research, it was the highlight of my time as a PhD student. Katriann Arja, for being a truly genuine and caring friend as well as an excellent life coach. Thank you for being a beacon of positivity and for lifting the spirits of everyone around you. Lastly, for our running sessions and discussions about happiness, Aitäh! Linda Lantz, my big sister at work, for taking me under your wing and making me feel at home. Thank you for trying to teach me everything from how to speak to how to run. Very few things make me as happy as baking pastries and treating you to them. Marcus Bäck, my brother from another mother, for your perpetual support, encouragement and most enjoyable company. Few people can relate to or understand me on a personal level as well as you can. VI Mathias Elgland, my doppelganger, for sharing all my peculiar interests. I have thoroughly enjoyed all our time together, from listening to Ludde to throwing flat circular objects around and everything in between. Anders Rexander, my former brother in arms, for all the enjoyable banter and hard-fought duels in various racket sports. The lab was never the same without you. Caroline Eriksson, my dear friend, for helping me break out of my shell. Few people have had such a positive impact on me as a person as you have. Tobias Abrahamsson for being around since the beginning...

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“…Brown and Zweifel 1 have shown that the hydroboration of asymmetric alkene yields the antiMarkownikoff addition product predominantly and that the addition takes place at β-carbon atom. Since the discovery of hydroboration reaction several attempts have been made to explain the reaction mechanism.…”

Section: Introductionmentioning

confidence: 99%

Hydroboration of Cyclopropane: A Transition State Study

Singh¹,

Thankachan²

2013

Chem Sci Trans

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Abstract:The hydroboration of cyclopropane has been investigated using the B3LYP density functional method employing several split-valence basis sets. It is shown that the reaction proceeds via a four-centered transition state. Calculations at higher levels of theory were also performed at the geometries optimized at the B3LYP level, but only slight changes in the barriers were observed. Structural parameters for the transition state are also reported.

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A Stereospecific Cis Hydration of the Double Bond in Cyclic Derivatives

Cited by 113 publications

References 0 publications

Arylboronic Acid Chemistry under Electrospray Conditions

Arylboronic Acid Chemistry under Electrospray Conditions

An insight into the metabolism of New Psychoactive Substances : Structural elucidation of urinary metabolites of synthetic cannabinoids and fentanyl analogues using synthesized reference standards

Hydroboration of Cyclopropane: A Transition State Study

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