Unsaturated diaziridines thermal cleavage possibilities: Disrotatory or conrotatory?

被引:0
作者
Arshadi, S. [1 ]
Forouzani, M. [1 ]
Qarepour, A. [1 ]
Karami, A. R. [2 ]
机构
[1] Univ Payame Noor, Dept Chem, Behshahr Unit, 7th Km Behshahr Gurgan Rd, Behshahr, Iran
[2] Shahid Rajaee Univ, Tehran, Iran
来源
COMPUTATIONAL CHEMISTRY AND APPLICATIONS IN ELECTRONICS | 2007年
关键词
diaziridines; azomethine imides; electrocyclic; thermal cleavage; conrotatory; IRC;
D O I
暂无
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Ab initio calculations are carried out at UB3LYP/6-311++G (3df, 2p) levels of theory, on electrocyclic thermal cleavage of four (R) derivatives of diaziridines, 1(X-R), to their corresponding (Z) and (E) azomethine imides (2(X-Z), 2(X-E), 3(X-Z) and 3(X-E)), where X = -H, -Me, -t-Bu and -Ph. Cleavage of 3(X-R) Series to 3(X-Z) (Path 3) emerged as the more favored, for producing the most stable products, 3(X-Z). In IRC calculations that were shown in Path 3 and 4, C-6-N-5 bond was cleavage, before reaching reaction rate determinating step (transition state).
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页码:52 / +
页数:4
相关论文
共 15 条
[1]   Diaziridines thermal cleavage possibilities: Disrotatory or conrotatory? [J].
Arshadi, S. ;
Rahimi, H. ;
Gasemi, A. ;
Sayyed-alangi, S. Z. .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2006, 770 (1-3) :7-12
[2]   Woodward-Hoffmann rule in the light of the principles of maximum hardness and minimum polarizability:: DFT and ab initio SCF studies [J].
Chattaraj, PK ;
Fuentealba, P ;
Gómez, B ;
Contreras, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (02) :348-351
[3]   Halogenated diazirines as photolabel mimics of the inhaled haloalkane anesthetics [J].
Eckenhoff, RG ;
Knoll, FJ ;
Greenblatt, EP ;
Dailey, WP .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (09) :1879-1886
[4]   The Woodward-Hoffmann-De Puy rule revisited [J].
Faza, ON ;
López, CS ;
Alvarez, R ;
de Lera, AR .
ORGANIC LETTERS, 2004, 6 (06) :905-908
[5]  
Frisch, 2016, GAUSSIAN16 REVISIONC
[6]   AN IMPROVED ALGORITHM FOR REACTION-PATH FOLLOWING [J].
GONZALEZ, C ;
SCHLEGEL, HB .
JOURNAL OF CHEMICAL PHYSICS, 1989, 90 (04) :2154-2161
[7]  
KASSAEE MZ, 2002, S J MOL STRUCT THEOC, V624, P69
[8]   Conformational stabilization of 1,3-benzodioxole: Anomeric effect by natural bond orbital analysis [J].
Moon, S ;
Kwon, Y ;
Lee, J ;
Choo, J .
JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (13) :3221-3225
[9]   REACTION OF ORGANO-LITHIUM COMPOUNDS WITH A TRIPHENYLCYCLOPROPYL DERIVATIVE - THE MATTER OF CYCLOPROPYL ANION RING-OPENING [J].
MULVANEY, JE ;
LONDRIGAN, ME ;
SAVAGE, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4592-4594
[10]   PRINCIPLE OF MAXIMUM HARDNESS [J].
PARR, RG ;
CHATTARAJ, PK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1854-1855