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Two syntheses of (+/-)-[2.2]paracyclophane-4-thiol have been accomplished in two and five steps, with overall yields of 46 and 31%, respectively, from [2.2]paracyclophane. The strategy involves two key reactions: (a) a lithium aluminium hydride reduction of the disulphide of [2.2]paracyclophane and (b) the use of a Newman-Kwart reaction for the conversion of [2.2]paracyclophane-4-ol to [2.2]paracyclophane-4-thiol.
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