{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T19:07:37Z","timestamp":1767985657018,"version":"3.49.0"},"reference-count":59,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2025,7,2]],"date-time":"2025-07-02T00:00:00Z","timestamp":1751414400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Science Foundation","award":["CHE-0744578"],"award-info":[{"award-number":["CHE-0744578"]}]},{"name":"National Science Foundation","award":["CHE-1265679"],"award-info":[{"award-number":["CHE-1265679"]}]},{"name":"National Science Foundation","award":["CHE-1337594"],"award-info":[{"award-number":["CHE-1337594"]}]},{"name":"National Science Foundation","award":["CHE-1429329"],"award-info":[{"award-number":["CHE-1429329"]}]},{"name":"University at Albany","award":["CHE-0744578"],"award-info":[{"award-number":["CHE-0744578"]}]},{"name":"University at Albany","award":["CHE-1265679"],"award-info":[{"award-number":["CHE-1265679"]}]},{"name":"University at Albany","award":["CHE-1337594"],"award-info":[{"award-number":["CHE-1337594"]}]},{"name":"University at Albany","award":["CHE-1429329"],"award-info":[{"award-number":["CHE-1429329"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We report the first syntheses\u2014from commercially available 3-chloro-2-fluoroprop-1-ene (9)\u2014of key garlic-derived compounds containing sp2-fluorine. We also report synthesis of fluoro-5,6-dihydrothiopyrans by trapping 2-fluorothioacrolein (15). Thus, difluoroallicin (12, S-(2-fluoro-2-propenyl) 2-fluoroprop-2-ene-1-sulfinothioate) is prepared by peracid oxidation of 1,2-bis(2-fluoro-2-propenyl)disulfane (11). S-2-Fluoro-2-propenyl-l-cysteine (2-fluorodeoxyalliin, 13), synthesized from cysteine and characterized by X-ray crystallography, is oxidized to its S-oxide, 2-fluoroalliin (22). The latter, with alliinase-containing powdered fresh garlic, gives a mixture of 12, allicin (1), and isomers of monofluoroallicin (23), indicating that 22 serves as a substrate for garlic alliinase. Upon heating, 12 generates transient 15, which dimerizes giving difluoro vinyl dithiins 6 and 7. Ethyl acrylate trapping of 15 affords 5- and 6-substituted 3-fluoro-5,6-dihydro-4H-thiopyrans (19 and 20). In 1,1,1,3,3,3-hexafluoro-2-propanol (HEFP) as solvent, 12 is converted into trifluoroajoene ((E,Z)-1-(2-fluoro-3-((2-fluoro-2-propenyl)sulfinyl)prop-1-en-1-yl)-2-(2-fluoro-2-propenyl)disulfane; 18). Liquid sulfur converts 11 to a (CH2=CFCH2)2Sn mixture (n = 4\u201315), characterized by UPLC-(Ag+)-coordination ion spray-mass spectrometry.<\/jats:p>","DOI":"10.3390\/molecules30132841","type":"journal-article","created":{"date-parts":[[2025,7,3]],"date-time":"2025-07-03T04:35:52Z","timestamp":1751517352000},"page":"2841","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Fluorinated Analogs of Organosulfur Compounds from Garlic (Allium sativum): Synthesis and Chemistry"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4668-1687","authenticated-orcid":false,"given":"Eric","family":"Block","sequence":"first","affiliation":[{"name":"Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5237-2373","authenticated-orcid":false,"given":"Benjamin","family":"Bechand","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7996-0658","authenticated-orcid":false,"given":"Sivaji","family":"Gundala","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5602-4015","authenticated-orcid":false,"given":"Abith","family":"Vattekkatte","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9457-7534","authenticated-orcid":false,"given":"Kai","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222, USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2025,7,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1950","DOI":"10.1021\/ja01239a048","article-title":"Allicin, the Antibacterial Principle of Allium sativum. 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