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A general synthetic route to highly twisted 1,1′-dinaphthopyrans from dinaphthofuran
Wang Bin 1 *,Li Minxiong 1,Xu Shansheng 2,Song Haibin 2,Wang Baiquan 2
1.College of Chemistry, Nankai University
2.College of Chemistry - Nankai University
*Correspondence author
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Funding: 教育部博士点基金(No.20030055001)
Opened online: 3 November 2006
Accepted by: none
Citation: Wang Bin ,Li Minxiong ,Xu Shansheng .A general synthetic route to highly twisted 1,1′-dinaphthopyrans from dinaphthofuran[OL]. [ 3 November 2006] http://en.paper.edu.cn/en_releasepaper/content/9243
 
 
The reaction of dinaphthofuran (1), lithium pieces (2.2 equiv), in dry ether led to a solution of the corresponding C,O-dilithiated intermediate 2 which, upon treatment with different ketones or aldehydes (0.8 equiv) at -78 oC, afforded, after hydrolysis and dehydration, highly twisted 1,1′-dinaphthopyrans 3 in good yields. The reaction undergoes reductive ring opening and cyclization, the intermediate diol 4c was isolated.
Keywords:Dinaphthofuran, 1,1′-Dinaphthopyran, Reductive ring opening
 
 
 

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