Computational Chemistry in the Undergraduate Laboratory: A Mechanistic Study of the Wittig Reaction

2014 ◽  
Vol 91 (12) ◽  
pp. 2182-2185 ◽  
Author(s):  
Birgit Albrecht
1988 ◽  
Vol 41 (8) ◽  
pp. 1243 ◽  
Author(s):  
AD Abell ◽  
BM Clark ◽  
WT Robinson

The structure of an isolated acyclic intermediate in the Wittig reaction between succinic anhydride and ethoxycarbonylmethylenetriphenylphosphorane has been shown by X-ray structure analysis and DEPT n.m.r .to be the phosphorane (4a) rather than the alternative phosphonium salt (4b). However, an intermediate was not observed in the Wittig reaction between the phosphorane (1b) and cyclic anhydrides. Both the stabilized phosphoranes (1a,b) react with succinic, phthalic and glutaric anhydrides stereoselectively to produce E enol lactones. Some mechanistic aspects are discussed. The assignment of the enol lactone stereochemistry was achieved by n.O.e. difference n.m.r. methods.


ChemInform ◽  
1989 ◽  
Vol 20 (6) ◽  
Author(s):  
H. YAMATAKA ◽  
K. NAGAREDA ◽  
Y. TAKAI ◽  
M. SAWADA ◽  
T. HANAFUSA

1988 ◽  
Vol 53 (16) ◽  
pp. 3877-3879 ◽  
Author(s):  
Hiroshi Yamataka ◽  
Katsushi Nagareda ◽  
Yoshio Takai ◽  
Masami Sawada ◽  
Terukiyo Hanafusa

2018 ◽  
Vol 270 ◽  
pp. 526-534 ◽  
Author(s):  
Pavel A. Abramov ◽  
Alexey A. Dmitriev ◽  
Kirill V. Kholin ◽  
Nina P. Gritsan ◽  
Marsil K. Kadirov ◽  
...  

2001 ◽  
Vol 120 (5) ◽  
pp. A145-A145
Author(s):  
C CHO ◽  
Y YE ◽  
E LIU ◽  
V SHIN ◽  
N SHAM

Planta Medica ◽  
2014 ◽  
Vol 80 (16) ◽  
Author(s):  
L Wang ◽  
L Shan ◽  
G Cui ◽  
Y Chen ◽  
J li ◽  
...  
Keyword(s):  

Sign in / Sign up

Export Citation Format

Share Document