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

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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. 
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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.
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