Acid-catalyzed rearrangement of [mn 2] propellanones

K Kakiuchi, K Itoga, T Tsugaru, Y Hato…

Index: Kakiuchi, Kiyomi; Itoga, Kazuo; Tsugaru, Toshinori; Hato, Yukinori; Tobe, Yoshito; Odaira, Yoshinobu Journal of Organic Chemistry, 1984 , vol. 49, # 4 p. 659 - 665

Full Text: HTML

Citation Number: 13

Abstract

The acid-catalyzed rearrangement of [mn 2] propellanones (m= 3-5, n= 3, 4) was studied to ascertain the effect of ring size on the mode of rearrangement. Propellanones 9 and 10, containing a fivemembered cycloalkanone ring, did not rearrange. Propellanones containing a six-or seven-membered cycloalkanone ring (11-14) rearranged smoothly to cyclopentanones 17a, 18, and 19 in a nonnucleophilic medium. In the presence of a ...