Lithium dimethylcuprate mixture with water

Iodo-3-methoxy-fr r 5-cyclo-octene (150 R = I) and 2-iodo-3-methoxy-trans-cyclonona-1,6-diene (151 R = I) have been prepared by silver perchlorate-catalysed rearrangement of 8,8-di-iodobicyclo[5,l,0]octane and 9,9-di-iodobicyclo[6,l,0]non-4-ene, respectively. Treatment of (150 R = I) with methyl-lithium then water, deuterium oxide, or methyl iodide, gave (150 R = H, D, or Me), respectively. Treatment of (151 R = I) with methyl-lithium then water gave a product mixture which contained cyclonona-l,2,6-triene as the major component, whereas treatment with methyl-lithium then methyl iodide gave (151 R = Me) in good yield. (151 R = H or D) were obtained from (151 R = I) using lithium dimethylcuprate then water or deuterium oxide. 

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