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Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes

✍ Scribed by Nakyen Choy; Chang-Sik Kim; Cynthia Ballestero; Leanne Artigas; Christian Diez; Frank Lichtenberger; Jed Shapiro; K.C Russell

Book ID
104210759
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
168 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of 4-substituted-1,2-diethylnylbenzenes were prepared (1a±f) and subjected to Bergman cyclization. Bulk cyclization proceeded to produce the corresponding 2-substituted naphthalenes (2a±f) in good yields (59±78%). Kinetic experiments show a linear free energy relationship between the cyclization rate and the Hammett s m substituent coecient and the Swain±Lupton ®eld and resonance parameters.

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