768-50-3Relevant articles and documents
Catalytic Multisite-Selective Acetoxylation Reactions at sp2 vs sp3 C-H Bonds in Cyclic Olefins
Zang, Zhong-Lin,Zhao, Sheng,Karnakanti, Shuklachary,Liu, Cheng-Lin,Shao, Pan-Lin,He, Yun
, p. 5014 - 5017 (2016/10/14)
The first Pd-catalyzed multisite-selective acetoxylation reactions are disclosed at an unactivated alkene sp2 C-H bond versus secondary allylic sp3 C-H bond in cyclic olefins via the modulation of directing groups. The different directing groups overcome the key challenge in differentiating C-H bonds and provide a new controlling approach for site-specific C-H activation. A wide variety of substrates are readily acetoxylated under operationally simple conditions. Mechanistic studies suggest that different Pd (IV) intermediates were involved in the multisite-selective acetoxylation reactions.
Stereoselective synthesis of β,γ-unsaturated ketones by acid-mediated Julia-type transformation from 2-(1-hydroxyalkyl)-1- alkylcyclopropanols
Nomura, Kenichi,Matsubara, Seijiro
experimental part, p. 1412 - 1414 (2009/04/06)
An efficient transformation of 2-(1-hydroxyalkyl)-1-alkylcyclopropanols, obtained from α,β-unsaturated ketones, to β,γ-unsaturated ketones was achieved by trifluoroacetic acid (TFA)-mediated reaction. Georg Thieme Verlag Stuttgart.
Acetylation de trimethylsilyl bicyclo(n,1,0)alcanes : nouvelles syntheses de l'acetyl cyclohexene-2 et d'acetyl bicyclo(n,1,0)alcanes
Ahra, M.,Grignon-Dubois, M.
, p. 820 - 824 (2007/10/02)
Acetylation of trimethylsilyl bicyclo(n,1,0)alkanes was studied using the CH3COCl/AlCl3 complex.The results showed that both larger cycle size (n = 3, 4 or 6) and stereochemistry of the substrate (SiMe3 group in endo or exo position) played a prominent role in the orientation of the reaction : depending upon the starting products, either bicyclic or ethylenic and/or chloro ketones were formed.The results can be rationalized in terms of steric hindrance considerations.They allowed us to propose a new convenient synthesis of acetyl bicyclo(n,1,0)alkanes and also of 1-acetyl 2-cyclohexene.
