Unusual photochemical behavior of 5-amino-endo-dicyclopentadien-3-ones Version 4.0

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Unusual photochemical behavior of 5-amino-endo-dicyclopentadien-3-ones
Bakkeren FJAD, Schroer F, de Gelder R, Klunder AJH, Zwanenburg B
TETRAHEDRON LETTERS 39: (51) 9527-9530 DEC 17 1998

Document type: Article

Language: English

Cited References: 30

Times Cited: 1

Abstract:
Irradiation of 5-amino-substituted endo-tricyclo[5.2.1.0(2.6)]deca-4,8-dien-3-ones 3 did not lead to the anticipated [pi(2) + pi(2)]-photocyclization to afford bridgehead 1,3-bishomocubyl amines 4. Instead an unexpected photoreduction of the norbornene C-8-C-9 double bond was observed, which based on D-labelling studies involves a photo-electron transfer process. The desired [pi(2) + pi(2)]-photo-cyclization furnishing 4-amido-substituted 1,3-bishomocubanones 7 could however be effected by N-acylation of the amino function in 3. (C) 1998 Elsevier Science Ltd. All rights reserved.

KeyWords Plus:
CRYSTAL-STRUCTURE

Addresses:
Klunder AJH, Catholic Univ Nijmegen, Dept Organ Chem, Toernooiveld, NL-6525 ED Nijmegen, Netherlands.
Catholic Univ Nijmegen, Dept Organ Chem, NL-6525 ED Nijmegen, Netherlands.
Catholic Univ Nijmegen, Dept Inorgan Chem, NL-6525 ED Nijmegen, Netherlands.
Catholic Univ Nijmegen, NSR Ctr Mol Struct Design & Synth, NL-6525 ED Nijmegen, Netherlands.

Publisher:
PERGAMON-ELSEVIER SCIENCE LTD, OXFORD

IDS Number:
146AF

ISSN:
0040-4039

Article 10 of 38