Art

J-GLOBAL ID：200902146678429518   Reference number：02A0358907

Preparation and Rearrangement of Arylhydroxymethano[3]orthocyclo[5](1,8)naphthalenophanes.

アリールヒドロキシメタノ[3]オルトシクロ[5](1,8)ナフタレノファンの合成および転位反応

Author (6)： ISOBE S (Kyushu Univ., Kasuga) ,  KUBO K (Kyushu Univ., Kasuga) ,  THIEMANN T (Kyushu Univ., Kasuga) ,  SAWADA T (Kyushu Univ., Kasuga) ,  YONEMITSU T (Kyushu Sangyo Univ., Fukuoka) ,  MATAKA S (Kyushu Univ., Kasuga)
Material： Bulletin of the Chemical Society of Japan  (Bull Chem Soc Jpn)
Volume： 75  Issue： 4  Page： 773-779  Publication year： Apr. 15, 2002 
JST Material Number： G0450A  ISSN： 0009-2673  CODEN： BCSJA8  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *cycloaddition ,...
Semi thesaurus term： *bridged compound

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JST classification (2)： Bridged tri-or more-cyclic carbocyclic compounds  (CF06110B) ,  Crystal structure of aromatic compounds  (BK08020F)

Substance index (10)： Phenyllithium ,  (8S)-8α,10α-(1,2-Xylylene)-8,9,10,11-tetrahydro-7H-cycloocta[de]naphthalene-9-one ,  (8S)-8α,10α-(1,2-Xylylene)-9-phenyl-8,9,10,11-tetrahydro-7H-cycloocta[de]naphthalene-9β-ol ,  (8S)-8α,10α-(1,2-Xylylene)-9-(4-methylphenyl)-8,9,10,11-tetrahydro-7H-cycloocta[de]naphthalene-9β-ol ,  (8S)-8α,10α-(1,2-Xylylene)-9-(2-methylphenyl)-8,9,10,11-tetrahydro-7H-cycloocta[de]naphthalene-9β-ol ,  (8S)-8α,12-[Methylene(1,2-phenylene)]-9β-(2-methylphenyl)-8,9,10,11-tetrahydro-9,10α-methano-7H-cycloocta[de]naphthalene ,  (9S)-1α,9α-(1,2-Xylylene)-9aβ-phenyl-1,2,8,9-tetrahydro-9aH-cyclopenta[cd]phenalene ,  (9S)-1α,9α-(1,2-Xylylene)-9aβ-(4-methylphenyl)-1,2,8,9-tetrahydro-9aH-cyclopenta[cd]phenalene ,  2-Methylphenyllithium ,  4-Methylphenyllithium

Reference (21)：

• 1) a) S. Isobe, M. Taniguchi, T. Sawada, T. Thiemann, T. Yonemitsu, and S. Mataka, J. Chem. Soc., Perkin Trans. 1, 1999, 2101.
•  b) S. Isobe, T. Thiemann, T. Sawada, T. Yonemitsu, and S. Mataka, Rep. Inst. Adv. Mat. Study, Kyushu Univ., 14, 7 (2000).
• 2) ¹³C NMR spectra in magic acid at a low temperature showed the chair-boat conformation of the phenyl- and 2-naphthyl-methyl cation. S. Prakash and M. Hachomy, private communication.
• 3) The rotational barrier of the benzyl cation has not been measured experimentally. Nevertheless, different calculations come to the result that the barrier is around 47 kcal/mol. — a) R. Glaser and D. Farmer, Chem. Eur. J., 3, 1244 (1997) [47.7 kcal/mol computed at MP4(sdtq)/6-31G*//MP2(full)/6-31G* + DVZPE(MP2(full)/6-31G*)].
•  b) A. E. Dorigo, Y. Li, and K. Houk, J. Am. Chem. Soc., 111, 6942 (1989) [45.4 kcal/mol (RHF/3-21G)].

Terms in the title (1)： 転位反応