Ab initiostudies of structural features not easily amenable to experiment. 22. Structural aspects of a long-chain hydrocarbon (n-nonane) and a study of the transferability of electronic effects through CC single bonds

1982 ◽  
Vol 3 (2) ◽  
pp. 269-272 ◽  
Author(s):  
J. N. Scarsdale ◽  
H. L. Sellers ◽  
Lothar Schäfer ◽  
Norman L. Allinger
Author(s):  
CLIFFORD C. LEZNOFF ◽  
ANNA M. D'ASCANIO ◽  
S. ZEKI YILDIZ

Lithium metal added to a solution of 4-neopentoxyphthalonitrile in 1-octanol or other long-chain primary alcohols at room temperature resulted in phthalocyanine formation at a reasonable rate in good yield, while preformed lithium 1-octanolate under the same conditions gave 2,9,16,23-tetraneopentoxyphthalocyanine, but in lower yield at a slower rate. The use of lower-molecular-weight alcohols slowly gave a phthalocyanine in lower yields. Reverse micelle formation when using long-chain alcohols is proposed as a possibility for enhanced phthalocyanine formation at room temperature. 2,9,16,23-Tetrasubstituted phthalocyanines and metallated phthalocyanines were prepared at room temperature from 4-neopentoxyphthalonitrile, 4-bis(4-methoxyphenyl)methoxyphthalonitrile, 4-[1-(4-ethoxy-3-methoxyphenyl)-1-phenyl]methoxyphthalonitrile and phthalonitrile using lithium 1-octanolate in 1-octanol or by the addition, to a solution of the phthalonitrile in ethanol, of calcium turnings or, to a solution of the phthalonitrile in methanol, of magnesium, zinc, iron or copper powder. The tetrasubstituted phthalocyanines produced exhibited a non-statistical distribution of regioisomers, indicating that electronic effects become important in room-temperature cyclotetramerization of phthalonitriles to phthalocyanines.


1975 ◽  
Vol 64 (4) ◽  
pp. 704-706 ◽  
Author(s):  
William C. Eckelman ◽  
Stephen M. Karesh ◽  
Richard C. Reba

Weed Science ◽  
1968 ◽  
Vol 16 (4) ◽  
pp. 541-544 ◽  
Author(s):  
G. W. Flint ◽  
J. J. Alexander ◽  
O. P. Funderburk

The vapor pressures of the four most common commercial low-volatile esters and a reference high-volatile ester of 2,4-dichlorophenoxyacetic acid (2,4-D) were determined by gas-liquid chromatography. The order of increasing volatility and the vapor pressure of these esters in mm of Hg at 187 C are as follows: isooctyl—2.7; 2-ethylhexyl—3.0; butoxy ethanol—3.9; propylene glycol butyl ether—3.9; and the reference, isopropyl—16.7. Extrapolations to 25 C support this ranking at working temperatures. Commercial esters of 2,4-D derived from long-chain hydrocarbon alcohols are in the same volatility range as the commercial esters containing an ether linkage.


Cell Reports ◽  
2019 ◽  
Vol 26 (9) ◽  
pp. 2451-2464.e5 ◽  
Author(s):  
Hyun Gi Kong ◽  
Hyun Ho Kim ◽  
Joon-hui Chung ◽  
JeHoon Jun ◽  
Soohyun Lee ◽  
...  

2014 ◽  
Vol 86 (6) ◽  
pp. 913-924 ◽  
Author(s):  
Saverio Florio ◽  
Leonardo Degennaro ◽  
Rosmara Mansueto ◽  
Biagia Musio ◽  
Filippo M. Perna ◽  
...  

AbstractThis paper focuses on α-lithiated oxazolinyloxiranes and oxazolinylaziridines, their generation, reactions, and synthetic applications. The ability of the oxazoline ring in providing stabilization to such α-heterosubstituted carbanions either through electronic effects and coordinative action has been stressed as well as the contribution to the configurational stability or instability of such species. IR spectroscopic data, multinuclear NMR investigations, and ab initio calculations planned to get insights on chemical properties and structural features have been carried out. A number of new reactions including alkylations, addition reactions, hydroxyalkylations, cyclopropanations, lactonizations, and rearrangements have been discovered, giving access to a variety of substances including: aziridinolactones, epoxylactones, aryl alkanones, polysubstituted cyclopropanes, cyclopropanefused lactones, dihydro-oxazoloisoquinolines, diversely functionalized oxazolines, and products that can be derived from them by synthetic elaboration.


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