Addition of arenesulphenyl chlorides to 2-methylenebicyclo[2.2.1]hept-5-ene: effect of increasing electron demand upon the rate and product determining transition states
Keyword(s):
The rates and products of addition of a series of sixteen arenesulphenyl chlorides to 2-methylenebicyclo[2.2.1]hept-5-ene, 7, and the E, Z isomeric 2-ethylidenebicyclo[2.2.1]hept-5-enes, 8 and 9, have been determined in methylene chloride solution. The major species from attack on 7 is always endo-3-arylthio-1-chloromethyltricyclo[2.2.1.02,6]heptane, the product of exo attack upon the endocyclic double bond with homoallylic participation of the exocyclic π system. No evidence was found for initial electrophilic attack upon the exocyclic double bond.
1994 ◽
Vol 98
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pp. 2844-2847
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1968 ◽
Vol 46
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pp. 2147-2157
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2007 ◽
Vol 42
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pp. 299-309
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1999 ◽
Vol 54
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pp. 113-116
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1975 ◽
Vol 37
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pp. 979-983
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