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[2+2] Photocycloaddition of 2‐Morpholinoprop‐2‐enenitrile to Perinaphthenone
Author(s) -
Döpp Dietrich,
Mohamed Shaaban K.,
ElKhawaga Ahmed
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20011219)84:12<3673::aid-hlca3673>3.0.co;2-k
Subject(s) - chemistry , adduct , benzene , singlet state , excitation , population , singlet oxygen , photochemistry , stereochemistry , oxygen , organic chemistry , atomic physics , excited state , physics , demography , sociology , electrical engineering , engineering
Perinaphthenone (=1 H ‐phenalen‐1‐one), known for efficient population of its T 1 ( π , π *) state and suggested as a standard sensitizer for singlet oxygen ( 1 Δg) formation, forms a single stereoisomer of a head‐to‐tail [2+2] photoadduct across its C(2)=C(3) bond with 2‐morpholinoprop‐2‐enenitrile in benzene by broad band UV excitation ( λ ≥280 nm). The reaction is advantageously run to low conversion of starting materials only. The structure of the adduct, especially the relative configuration at C(9), has been derived from 1 H‐NMR data including NOE signal enhancement studies.