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7857398 
Journal Article 
Photoinitiated reaction of beta -bromonaphthalene with pinacolone ion in DMSO 
Chen, ZB; Zhao, LY; Zhang, Z 
2000 
1 
Chinese Chemical Letters
ISSN: 1001-8417
EISSN: 1878-5964 
11 
11 
945-948 
English 
WOS:000090141600002 
The photoinitiated reaction of β-bromonaphthalene with excess pinacolone enolate does not yield expected normal SRN1 product 1-β-naphthyl-3,3-dimethyl-2-butanone, 3, but a more complex molecule 2,2-dimethyl-5-(1',1'-dimethylethyl)-6-β-naphthyl-5-hexene-3-one, 4, deriving from it. The reaction is inhibited by m-dinitrobenzene and do not occur in the absence of light. Structure analysis of the product, along with other evidence, indicates a mechanism for this reaction, where addition of a further pinacolone molecule to carbonyl group of 3 and subsequent elimination of a water molecule would afford product 4, once the SRN1 substitution product 3 has formed. 
S(RN)1 reaction; beta -bromonaphthalene; pinacolone enolate; addition reaction 
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