{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,27]],"date-time":"2026-09-27T05:17:43Z","timestamp":1790486263992,"version":"4.1.0"},"reference-count":84,"publisher":"Wiley","issue":"44","license":[{"start":{"date-parts":[[2016,9,15]],"date-time":"2016-09-15T00:00:00Z","timestamp":1473897600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"crossref"}]},{"name":"DFG"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2016,10,24]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    \u03b2\u2010(3\u2010Iodopropoxy)\u2010substituted \u03b1,\u03b2\u2010unsaturated lactams, lactones, and cycloalkenones (eight examples) underwent reductive radical reactions in a dichloromethane solution of\n                    <jats:italic>N,N<\/jats:italic>\n                    \u2010diisopropylethylamine (H\u00fcnig's base) upon irradiation with visible light (\n                    <jats:italic>\u03bb<\/jats:italic>\n                    =419\u2005nm). Apart from plain reduction reactions (hydro\u2010de\u2010iodination), a significant degree of cyclization was observed in three cases. In parallel to the conversion of the substrates, the formation of intensely colored by\u2010products was observed. Based on mass spectrometric evidence and upon comparison with known compounds, the by\u2010products were identified as cyanine dyes. Their formation supports the hypothesis that irradiation of dichloromethane solutions of H\u00fcnig's base leads to the formation of radicals, which in turn can either initiate a radical reaction or combine with cyanine precursors. It was shown by deuterium\u2010labelling experiments, that one equivalent of dichloromethane is incorporated into the cyanine dyes and that the reductive quenching of radical intermediates is at least partially due to hydrogen abstraction from the solvent. As a consequence, a reductive cyclization of the starting materials is favored in CD\n                    <jats:sub>2<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    solutions as shown for two \u03b2\u2010(3\u2010iodopropoxy)\u2010substituted tetronates, which underwent in dichloromethane almost exclusive reduction, but gave predominantly the cyclization products in CD\n                    <jats:sub>2<\/jats:sub>\n                    Cl\n                    <jats:sub>2<\/jats:sub>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/chem.201603303","type":"journal-article","created":{"date-parts":[[2016,9,15]],"date-time":"2016-09-15T04:49:27Z","timestamp":1473914967000},"page":"15921-15928","source":"Crossref","is-referenced-by-count":35,"title":["Radical Reactions Induced by Visible Light in Dichloromethane Solutions of H\u00fcnig's Base: Synthetic Applications and Mechanistic Observations"],"prefix":"10.1002","volume":"22","author":[{"given":"Alexander","family":"B\u00f6hm","sequence":"first","affiliation":[{"name":"Department Chemie and Catalysis Research Center (CRC) Technische Universit\u00e4t M\u00fcnchen  Lichtenbergstra\u00dfe 4 85747 Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1342-0202","authenticated-orcid":false,"given":"Thorsten","family":"Bach","sequence":"additional","affiliation":[{"name":"Department Chemie and Catalysis Research Center (CRC) Technische Universit\u00e4t M\u00fcnchen  Lichtenbergstra\u00dfe 4 85747 Garching Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,9,15]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"Selected 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