Ir-Catalyzed ring-opening of oxa(aza)benzonorbornadienes with water or alcohols

2019 ◽  
Vol 6 (8) ◽  
pp. 1151-1156 ◽  
Author(s):  
Xin Yang ◽  
Wen Yang ◽  
Yongqi Yao ◽  
Yingying Deng ◽  
Dingqiao Yang

A highly efficient Ir-catalyzed ring-opening reaction of oxa(aza)benzonorbornadienes with water was firstly developed, which afforded a mild access to substituted dihydronaphthalene products with excellent yields (up to 99%) within 30 min.

2007 ◽  
Vol 31 (12) ◽  
pp. 2041 ◽  
Author(s):  
Hui-quan Xiao ◽  
Xing-zhong Shu ◽  
Ke-gong Ji ◽  
Chen-ze Qi ◽  
Yong-min Liang

2018 ◽  
Vol 15 (3) ◽  
pp. 605-612 ◽  
Author(s):  
Qi Wang ◽  
Zhang-Gui Hou ◽  
Bo Zhang ◽  
Jian Liu ◽  
Wei-Yu Song ◽  
...  

1980 ◽  
Vol 21 (33) ◽  
pp. 3209-3212 ◽  
Author(s):  
Isao Kuwajima ◽  
Showay Hoshino ◽  
Toshihiko Tanaka ◽  
Makoto Shimizu

2012 ◽  
Vol 33 (9) ◽  
pp. 848-855 ◽  
Author(s):  
Aurélie Laquièvre ◽  
Naomi S. Allaway ◽  
Joël Lyskawa ◽  
Patrice Woisel ◽  
Jean-Marc Lefebvre ◽  
...  

2018 ◽  
Author(s):  
Veejendra Yadav ◽  
Dasari L V K Prasad ◽  
Arpita Yadav ◽  
Maddali L N Rao

<p>The torquoselectivity of conrotatory ring opening of 3-carbomethoxycyclobutene is controlled by p<sub>C1C2</sub>→s*<sub>C3C4</sub> and s<sub>C3C4</sub>→p*<sub>CO</sub> interactions in the transition state in a 4-electron process as opposed to only s<sub>C3C4</sub>→p*<sub>CO</sub> interaction in an apparently 8-electron event in 3-carbomethoxy-1,2-benzocyclobutene. The ring opening of 3-carbomethoxy-1,2-benzocyclobutene is sufficiently endothermic. We therefore argue that the reverse ring closing reaction is faster than the forward ring opening reaction and, thus, it establishes an equilibrium between the two and subsequently allows formation of the more stable species <i>via</i> outward ring opening reaction. Application of this argument to 3-dimethylaminocarbonyl-1,2-benzocyclobutene explains the predominantly observed inward opening.</p>


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