A comparative study of photoinduced isomerizations between 1-exo- and 1-endo-cyano-1a,7b-dihydro-1H-cyclopropa(a)naphthalenes.
スポンサーリンク
概要
- 論文の詳細を見る
The titled compunds 1-<I>exo</I>-Cyano-1a,7b-dihydro-1<I>H</I>-cyclopropa[<I>a</I>]naphthalenes(<B>8a</B>), 1-<I>endo</I>-Cyano-1a,7b-dihydro-1<I>H</I>-cyclopropa[<I>a</I>]naphthalenes(<B>8b</B>), were photolyzed in several solvents. The results were: (1) The isomerization proceeded faster in aprotic nonpolar solvents than in polar ones. (2) The 1-<I>endo</I> derivative (<B>8b</B>) rearranged faster than the 1-<I>exo</I>-isomer (<B>8a</B>). (3) <B>8b</B> was isomerized through Berson-Willcott rearrangement by the fission of bonds C<SUB>1</SUB>–C<SUB>7b</SUB> and C<SUB>1</SUB>–C<SUB>1a</SUB>, while <B>8a</B> gave 1-cyanomethylnaphthalene (<B>5b</B>) as a main product. (4) Examination with an optically active 1-<I>exo</I> derivative (<B>8a</B>) showed that the <I>exo</I>-<I>endo</I> interconversion occured by the simultaneous two centered (30%) and one centered (70%) epimerization.
- 公益社団法人 日本化学会の論文
著者
-
Kato Masahiko
Faculty Of Engineering Hiroshima University
-
Miwa Toshio
Faculty of Science, Osaka City University
-
Kobayashi Hisako
Faculty of Science, Osaka City University
関連論文
- Simulation of Cracking Patterns in Sprayed Coating under Equi-Biaxial Tension
- The isolation,characterization,and isomerization of cis- and trans-bis(benzonitrile)dichloroplatinum(II).
- The relative rates of ene reaction of benzyne with cyclic olefins: The stereochemical course.
- One pot synthesis of substituted tropones from 7,7-dihalo-2,3-(or 3,4-)epoxybicyclo(4.1.0)heptane derivatives.
- A comparative study of photoinduced isomerizations between 1-exo- and 1-endo-cyano-1a,7b-dihydro-1H-cyclopropa(a)naphthalenes.
- Synthesis of Benzo(1,2:4,5)dicycloheptene-1,9-dione via 6,7,12,13-Tetrahydro-7,12-methano-3H-cycloheptacyclodecene-3,14-dione and Its Protonation Behavior.
- The Birch Reduction of Heterocyclic Carboxylic Acids. I. The Birch Reduction of 3-Furoic Acid
- The Photochemical Decomposition of Benzenediazonium o-Carboxylate in Several Solvents
- Branched-chain sugars. II. Synthesis of methyl 5-deoxy-3-C-hydroxymethyl-2,3-O-isopropylidene-.BETA.-DL-lyxo-furanoside (dihydrostreptose) and ribofuranoside derivatives.