Transannular photochemical ring closure of 1, 2, 5, 6-tetramethylenecyclooctane as a synthetic route to small-ring propellanes

WT Borden, IL Reich, LA Sharpe…

Index: Borden,W.T. et al. Journal of Organic Chemistry, 1975 , vol. 40, p. 2438 - 2442

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Citation Number: 16

Abstract

The synthesis of 2, 6-dimethylene [3.3. 2] propellane (4) in three steps and 12% overall yield from allene dimer 1 is reported. The key reaction is the formation of 4 by transannular photochemical ring closure of 1, 2, 5, 6-tetramethylenecyclooctane (3). A chemical separation of 4 from isomers that are carried through the synthesis is described, which makes the purification of the intermediates (1-3) unnecessary. Compound 4 has been ...