Photochemical transformation .79. [6+6]-photocycloadditions in ''face-to-face'' benzo/pyridazino systems en route to azapagodanes (azadodecahedranes)

被引：11

作者：

Mathew, T ^{[1
]}

Keller, M ^{[1
]}

Hunkler, D ^{[1
]}

Prinzbach, H ^{[1
]}

机构：

[1] UNIV FREIBURG, CHEM LAB, INST ORGAN CHEM & BIOCHEM, D-79104 FREIBURG, GERMANY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 26期

关键词：

D O I：

10.1016/0040-4039(96)00895-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In two very proximate syn-periplanar (''face-to-face'') benzo/pyridazino systems (shortest pi,pi-distances of ca. 3.0 Angstrom, X-ray), photoequilibration (ratio ca. 2:1) with the cyclobutane-photo[6+6]cycloadducts has been installed by 254 nm irradiation. The hetarene/arene ''dimers'' are thermally persistent enough as to allow pagodane formation through the cycloaddition of dienophiles. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：4491 / 4494

页数：4

共 29 条

[1] FORBIDDEN REACTIONS - [2 + 2] CYCLOREVERSION OF RIGID CYCLOBUTANES [J].

DOERING, WV ;

ROTH, WR ;

BREUCKMANN, R ;

FIGGE, L ;

LENNARTZ, HW ;

FESSNER, WD ;

PRINZBACH, H .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01) :1-9

[2] PI-FACIAL STEREOSELECTIVITY IN THE DIELS-ALDER REACTION .4. THE DIRECTING INFLUENCE OF PROXIMATE UNSATURATION [J].

FESSNER, WD ;

SCHEUMANN, K ;

PRINZBACH, H .

TETRAHEDRON LETTERS, 1991, 32 (42) :5939-5942

[3] PI-FACIAL STEREOSELECTIVITY IN THE DIELS-ALDER REACTION .3. AN UNSYMMETRICALLY BIRDCAGE-ANNULATED CYCLOHEXADIENE [J].

FESSNER, WD ;

GRUND, C ;

PRINZBACH, H .

TETRAHEDRON LETTERS, 1991, 32 (42) :5935-5938

[4] DOMINO AND PINCER CYCLO-ADDITIONS WITH SYN-O,O'-DIBENZENES SCOPE AND PI-FACIAL STEREOSELECTIVITY [J].

FESSNER, WD ;

GRUND, C ;

PRINZBACH, H .

TETRAHEDRON LETTERS, 1989, 30 (24) :3133-3136

[5]

FESSNER WD, 1990, CAGE HYDROCARBONS, P353

[6] DOMINANCE OF THROUGH-BOND INTERACTION IN A SYN-TRICYCLO[6.4.0.02,7]DODECATETRAENE MOIETY [J].

GLEITER, R ;

ZIMMERMANN, H ;

FESSNER, WD ;

PRINZBACH, H .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (09) :3856-3860

[7]

GOLDMAN NL, 1968, TETRAHEDRON LETT, P3951

[8]

GRUND C, 1984, THESIS U FREIBURG

[9]

HAIDER N, 1994, ACTA CHIM SLOV, V41, P205

[10] LAYERED COMPOUNDS .78. PHOTODIMERIZATION OF BENZENES IN STRAINED DIHETERA[3.3]METACYCLOPHANES [J].

HIGUCHI, H ;

KOBAYASHI, E ;

SAKATA, Y ;

MISUMI, S .

TETRAHEDRON, 1986, 42 (06) :1731-1739

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