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m-Bicyclo[5.1.0]oct-5-en-3-yl tosylate (c/í-1-OTs) exists in two conformational forms that solvolyze by independent pathways. The less stable (saddle) conformer (2) solvolyzes with double bond participation to form cis-1 (corresponding to retained starting material) and various hydride-shifted materials. The more stable (boat-chair) conformer 3 solvolyzes with cyclopropane participation to give the cz'j-bicyclo[5.1.0]oct-4-en-3-yl ester (cis-7). Quantitative product analysis indicates that about 80 % of the reaction occurs by double bond participation and 20% by cyclopropane participation. The study thus furnishes a direct comparison of the two forms of participation under competitive circumstances.(16) We are indebted to Professor John Grutzner, Purdue University, for these deuterium spectra, taken on a Varían XL-100.

chloro-2,2-diphenylcyclopropane, [a] 26d -64.8°(c 1.0, CHClg), prepared from acid, [<*]"« -82.1°, 93.9% optically pure, 150 mg of sodium amide, and 9 ml of benzene was stirred at reflux under nitrogen for 20 hr. Ice water was added and the solution was washed with water until the washings were neutral, dried, concentrated, and subjected to preparative tic on silica gel using benzene-hexane (1:1). The band with the highest Ri value weighed 18 mg and proved to be (-)-(fí)-l-chloro-2,2-diphenylcyclopropane based on nmr spectrum and elemental analysis:

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Die aus Benzoesäure (I) durch Umsetzung mit Na/Äthanol erhaltene 1,4‐Dihydrobenzoesäure (IIa) liefert nach Umwandlung in den Methylester (IIb) durch Diazomethan bei der Simmons‐Smith‐Reaktion mit Methylenjodid‐ Zn/Cu den tricyclischen Ester (IIIa), der zur freien Säure (IIIb) verseift und dann durch Bleitetraacetat zum Acetat (IVa) abgebaut wird, aus dem mit Lithiumalanat das freie Carbinol (IVb) entsteht.