Reactions of 1,3-Dehydroadamantane with Some Aromatic Disulfides

摘要

The reactions of some propellanes I-IV with disulfides are known [1-3]. For example, [l.l.l]propellane I reacts with diphenyl disulfide when heated [1] or by the photochemical initiation via a free-radical mechanism [2]. An asymmetric [4.4.1]propellane, 2,3-methano-2,4-didehydroadamantane II, reacts slowly, but selectively, in deuterated benzene with dimethyl disulfide to form 2,4-bis(methylthio)-2,4-methanoproto-adamantane [3]. No formation of other products was observed that would confirm the free-radical mechanism of this reaction.