Theoretical Studies of 5-exo Selective Intramolecular Cyclization of O-Alkynylbenzoic Acid Catalyzed by Organic Base

Heterocycles ◽  
2007 ◽  
Vol 74 (1) ◽  
pp. 819 ◽  
Author(s):  
Masahiro Terada ◽  
Masahiro Yamanaka ◽  
Chikashi Kanazawa
1982 ◽  
Vol 47 (8) ◽  
pp. 2280-2290 ◽  
Author(s):  
Helena Velgová ◽  
Jorga Smolíková ◽  
Antonín Trka ◽  
Antonín Vítek

Acid-catalyzed intramolecular cyclization of 6,7-dihydroxy-3α,5-cyclo-6,7-seco-5α-androstan-17-one (VII), 5,7-dihydroxy-3,5-methylene-5,7-secoandrostan-17-one and 5,7-dihydroxy-3β,5-cyclo-5,7-seco-A-homo-5β-androstan-17-one (XIII) in benzene and dioxane was investigated. The main cyclization products were 3,5-methylene-6-oxaandrostan-17-one (I) and/or 3β,5-cyclo-6-oxa-A-homo-5β-androstan-17-one (VIII). In the case of VI and VII the ratio of I and VIII was solvent-dependent: in benzene more VIII was formed than in dioxane. The mass spectra of I and VIII were almost identical and corresponded to the structure VIII.


2015 ◽  
Vol 41 (12) ◽  
pp. 10125-10135 ◽  
Author(s):  
Shangyou Xiao ◽  
Guang Xu ◽  
Gang Chen ◽  
Xiaojing Mu ◽  
Zhitao Chen ◽  
...  

ACS Omega ◽  
2022 ◽  
Author(s):  
In Seok Oh ◽  
Ye Ji Seo ◽  
Ji Young Hyun ◽  
Hwan Jung Lim ◽  
Duck-Hyung Lee ◽  
...  

2014 ◽  
Vol 10 ◽  
pp. 1032-1036 ◽  
Author(s):  
Masaaki Yoshifuji ◽  
Shigekazu Ito

The intramolecular C–H insertion of the Mes*-substituted phosphanylidenecarbene [Mes*P=C:] (Mes* = 2,4,6-t-Bu3C6H2) and physicochemical properties of the cyclized product, 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene were studied based on ab initio calculations. Whereas the alternative Fritsch–Buttenberg–Wiechell-type rearrangement requires almost no activation energy, the intramolecular cyclization needs an activation energy of 12.3 kcal/mol at the MP2(full)/6-31G(d) condition. DFT calculations supported that the optimized structure of the cyclization product of Mes*P=C: suggests remarkable conjugation effects between the nearly coplanar P=C skeleton and the aryl moiety.


2016 ◽  
Vol 47 (1) ◽  
pp. 44-52 ◽  
Author(s):  
Almir S. Gazizov ◽  
Andrey V. Smolobochkin ◽  
Ekaterina A. Anikina ◽  
Julia K. Voronina ◽  
Alexander R. Burilov ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document