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The 1,3-dipolar cycloaddition of adamantylidenefulvene (1) with 2equiv of nitrile oxides 2a–d gave 1/1 cycloadducts, 3a–d and 4a–d, as the major products, and four other 1/2 minor cycloadducts 5–8a,b. The ratios of 1/1 cycloadducts 3a–d to 4a–d in THF solution were about 1/1 in the four different nitrile oxides 2a–d studied and microwave was found to accelerate the reactions and enhance their yields...
Sodium borohydride reduction reactions on 4-X-adamantan-2-ones (where X=ethyleneketal 11, ethylenethioketal 12, and methylene 15) were studied, which gave Z-alcohols 16 and 17 (from en-face attack) as the predominant products for ketones 11 and 12, but gave 1:1 mixture of Z- and E-18 alcohols for ketone 15. The en/zu face selectivity of 15 in sodium borohydride reduction was enhanced to 32/68 in β-CD...
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