Articles | Volume 23, issue 14
https://doi.org/10.5194/acp-23-7859-2023
https://doi.org/10.5194/acp-23-7859-2023
Technical note
 | 
17 Jul 2023
Technical note |  | 17 Jul 2023

Technical note: Improved synthetic routes to cis- and trans-(2-methyloxirane-2,3-diyl)dimethanol (cis- and trans-β-isoprene epoxydiol)

Molly Frauenheim, Jason D. Surratt, Zhenfa Zhang, and Avram Gold

Related authors

Simulated reductions in Heterogeneous Isoprene Epoxydiol Reactive Uptake from aerosol morphology in the contiguous United States using the Community Multiscale Air Quality Model (CMAQv5.3.2)
Sara L. Farrell, Quazi Z. Rasool, Havala O. T. Pye, Yue Zhang, Ying Li, Yuzhi Chen, Chi-Tsan Wang, Haofei Zhang, Ryan Schmedding, Manabu Shiraiwa, Jaime Greene, Sri H. Budisulistiorini, Jose L. Jimenez, Weiwei Hu, Jason D. Surratt, and William Vizuete
EGUsphere, https://doi.org/10.5194/egusphere-2025-2253,https://doi.org/10.5194/egusphere-2025-2253, 2025
This preprint is open for discussion and under review for Atmospheric Chemistry and Physics (ACP).
Short summary
Hygroscopicity of Isoprene-Derived Secondary Organic Aerosol Mixture Proxies: The Importance of Solute Diffusion and Salting-In Effects
Nahin Ferdousi-Rokib, Stephanie Jacoby, N. Cazimir Armstrong, Alana Dodero, Martin Changman Ahn, Ergine Zephira Remy, Zhenfa Zhang, Avram Gold, Joseph L. Woo, Yue Zhang, Jason D. Surratt, and Akua A. Asa-Awuku
EGUsphere, https://doi.org/10.5194/egusphere-2025-1935,https://doi.org/10.5194/egusphere-2025-1935, 2025
Short summary
Ice-nucleating properties of glassy organic and organosulfate aerosol
Christopher N. Rapp, Sining Niu, N. Cazimir Armstrong, Xiaoli Shen, Thomas Berkemeier, Jason D. Surratt, Yue Zhang, and Daniel J. Cziczo
Atmos. Chem. Phys., 25, 5519–5536, https://doi.org/10.5194/acp-25-5519-2025,https://doi.org/10.5194/acp-25-5519-2025, 2025
Short summary
Composition and sources of carbonaceous aerosol in the European Arctic at Zeppelin Observatory, Svalbard (2017 to 2020)
Karl Espen Yttri, Are Bäcklund, Franz Conen, Sabine Eckhardt, Nikolaos Evangeliou, Markus Fiebig, Anne Kasper-Giebl, Avram Gold, Hans Gundersen, Cathrine Lund Myhre, Stephen Matthew Platt, David Simpson, Jason D. Surratt, Sönke Szidat, Martin Rauber, Kjetil Tørseth, Martin Album Ytre-Eide, Zhenfa Zhang, and Wenche Aas
Atmos. Chem. Phys., 24, 2731–2758, https://doi.org/10.5194/acp-24-2731-2024,https://doi.org/10.5194/acp-24-2731-2024, 2024
Short summary
Trends, composition, and sources of carbonaceous aerosol at the Birkenes Observatory, northern Europe, 2001–2018
Karl Espen Yttri, Francesco Canonaco, Sabine Eckhardt, Nikolaos Evangeliou, Markus Fiebig, Hans Gundersen, Anne-Gunn Hjellbrekke, Cathrine Lund Myhre, Stephen Matthew Platt, André S. H. Prévôt, David Simpson, Sverre Solberg, Jason Surratt, Kjetil Tørseth, Hilde Uggerud, Marit Vadset, Xin Wan, and Wenche Aas
Atmos. Chem. Phys., 21, 7149–7170, https://doi.org/10.5194/acp-21-7149-2021,https://doi.org/10.5194/acp-21-7149-2021, 2021
Short summary

Cited articles

Armstrong, N. C., Chen, Y., Cui, T., Zhang, Y., Christensen, C., Zhang, Z., Turpin, B. J., Chan, M.N., Gold, A., Ault, A. P., and Surratt, J. D.: Isoprene epoxydiol-derived sulfated and nonsulfated oligomers suppress particulate mass loss during oxidative aging of secondary organic aerosol, Environ. Sci. Technol., 56, 16611–16620, https://doi.org/10.1021/acs.est.2c03200, 2022. 
Bates, K. H., Crounse, J. D., St Clair, J. M., Bennett, N. B., Nguyen, T. B., Seinfeld, J. H., Stoltz B. M., and Wennberg, P. O.: Gas phase production and loss of isoprene epoxydiols, J. Phys. Chem. A, 118, 1237–1246, https://doi.org/10.1021/jp4107958, 2014. 
Bates, K. H., Nguyen, T. B., Teng, A. P., Crounse, J. D., Kjaergaard, H. G., Stoltz, B. M. Seinfeld, J. H., and Wennberg, P. O.: Production and fate of C4 dihydroxycarbonyl compounds from isoprene oxidation, J. Phys. Chem. A, 120, 106–117, https://doi.org/10.1021/acs.jpca.5b10335, 2016. 
Bloomfield, J. J. and Lee, S. L.: Control of lithium aluminum hydride reduction of cyclic dicarboxylic acid anhydrides to produce 7-lactones or diols, J. Org. Chem., 32, 3919–3924, 1967. 
Budisulistiorini, S. H., Li, X., Bairai, S. T., Renfro, J., Liu, Y., Liu, Y. J., McKinney, K. A., Martin, S. T., McNeill, V. F., Pye, H. O. T., Nenes, A., Neff, M. E., Stone, E. A., Mueller, S., Knote, C., Shaw, S. L., Zhang, Z., Gold, A., and Surratt, J. D.: Examining the effects of anthropogenic emissions on isoprene-derived secondary organic aerosol formation during the 2013 Southern Oxidant and Aerosol Study (SOAS) at the Look Rock, Tennessee ground site, Atmos. Chem. Phys., 15, 8871–8888, https://doi.org/10.5194/acp-15-8871-2015, 2015. 
Download
Short summary
We report synthesis of the isoprene-derived photochemical oxidation products trans- and cis-β-epoxydiols in high overall yields from inexpensive, readily available starting compounds. Protection/deprotection steps or time-consuming purification is not required, and the reactions can be scaled up to gram quantities. The procedures provide accessibility of these important compounds to atmospheric chemistry laboratories with only basic capabilities in organic synthesis.
Share
Altmetrics
Final-revised paper
Preprint