Journal of Organic Chemistry p. 4725 - 4729 (1985)
Update date:2022-08-03
Topics:
Osei-Twum, Emmanuel Y.
Warkentin, John
Thermolysis of α-hydroperoxy diazenes 1a-1c (Me2C(OOH)N=NR: 1a, R = CH2CF3; 1b, R = CH2CH2OCH3; 1c, R = CH2CH2OC6H5) at 50 deg C in benzene containing norbornene or in neat norbornene affords exo-(2R)-norbornane and exo-norbornene epoxide as major products and exo,exo-(2R)-3-hydroxynorbornane as a minor product.The reaction kinetics and the effects of deuteration of the hydroperoxy function on the distribution of products points to a radical chain process for the hydroalkylation and for the epoxidation.The other major product is formed by a competitive radical chain reaction.
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