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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 5
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Original Articles

Synthesis of Adamantane Derivatives. Xxiii. Facile Photo-Ring-Cleavage of 4-Homoadamantanone to Bicyclo[3.3.1] -Nonan-3 -Endo-Acetate

Tadashi Sasaki Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan, 464
,
Shoji Eguchi Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan, 464
&
Masato Mizutani Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan, 464
Pages 369-373 | Received 28 Aug 1973, Published online: 05 Dec 2006
 
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Abstract

Type I (α-) and II cleavages are two of the best known photochemical processes of alkanone.2 Extensive and intensive investigations have been done on both types of reactions in order to clarify the influence of structural changes on the reactivity, specificity, and efficiency of photoreactions of alkanones.3 The type I cleavage of medium-ring alkanones is believed to produce a radical pair, the fate of which will be determined by the ready formation of transition states for transfer of Ha, Hb, and recyclization. We now wish to report

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