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<jats:title>Abstract</jats:title><jats:p>The photocycloaddition of benzothiazole‐2‐thiones to electron‐rich and aryl‐substituted alkenes are described. Irradiation of <jats:italic>N</jats:italic>‐unsubstituted benzothiazole‐2‐thione (<jats:bold>1</jats:bold>) in the presence of alkenes <jats:bold>3</jats:bold> gave 2‐(2′‐mercaptoalkyl)benzothiazoles <jats:bold>4</jats:bold>, and 2‐substituted benzothiazoles <jats:bold>5</jats:bold> and <jats:bold>6</jats:bold> (in the case of <jats:bold>3a</jats:bold> and <jats:bold>3h</jats:bold>, resp.) through the ring cleavage of an intermediate 2‐aminothietane (<jats:italic>Schemes 1</jats:italic> and <jats:bold>3</jats:bold>). The latter was formed by [2+2] cycloaddition of the CS bond of <jats:bold>1</jats:bold> and the CC bond of <jats:bold>3</jats:bold>. Irradiation of <jats:italic>N</jats:italic>‐methylbenzothiazole‐2‐thione (<jats:bold>2</jats:bold>) and 2‐methylpropene (<jats:bold>3a</jats:bold>) gave the spiro‐1,3‐dithiane <jats:bold>8</jats:bold>, 1,2,6‐benzodithiazocin‐5‐one <jats:bold>9</jats:bold>, and disulfide <jats:bold>10</jats:bold>. The structure of <jats:bold>9</jats:bold> was established by X‐ray crystal‐structure analysis.</jats:p>
収録刊行物
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- Helvetica Chimica Acta
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Helvetica Chimica Acta 77 981-987, 1994-06-29
Wiley
