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Photochemical cycloaddition of an aromatic ketone to a 1-alkynyl ether. Kinetics and mechanism

✍ Scribed by H. Polman; J.P.B. Baaij; H.J.T. Bos

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 477 KB
Volume: 98
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19790980408

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✦ Synopsis

Abstract

In this paper kinetics and mechanism of the photoaddition of 10,11‐dihydro‐5__H__‐dibenzo‐[a,d]cyclohepten‐5‐one (dibenzosuberone, 4) to 1‐methoxy‐1‐propyne (5) with the formation of the unsaturated ester 8, are studied. In benzene at 25.0°C a limiting quantum yield Φ = 0.04 was found. The rate constant k~2~ of the addition of triplet ketone 4 to ground state 5 amounted to 1.9 · 107^7^ l.mol^−1^,s^−1^. The unexpected regiospecificity is not caused by attack of triplet alkyne on ground state ketone. The low quantum yield is mainly caused by the high revertibility of the addition reaction. The intermediacy of a triplet exciplex is discussed.

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## Introduction During the course of these studies, we have found that bis(4-aminophenyl) ether, a weakly basic aromatic diamine, together with tetrafunctional pyromel-Aromatic polyimides have been well-known since the litic acid, could form readily the salt monomer with 1 : early 1960s as the mos