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• W2111632015 abstract "The minor product, 4-protoadamantene (5), from the gas phase pyrolysis of 2-adamantyl mesylate (3) was shown by labelling experiments not to arise from the major product, 2,4-dehydroadamantane (4), but rather by a concerted process (homo-retroene reaction). In the formation of 4, 1,3-elimination is favored by at least a 92:8 margin over a competitive route involving α-elimination to a carbene and then C-H insertion. Equatorial and axial 2-noradamantyl mesylates pyrolyze to give predominantly 4-brendene (11) and triaxane (12), respectively, as required by concerted 1,3-eliminations, and not by an ion pair mechanism. The cross-over product appears in each case to result from the epimerizarion of the starting material by a wall-catalyzed process. In agreement with the results of the noradamantyl substrates, pyrolysis of 3-diamantyl mesylate (16) gave results which suggest that product stability helps to determine the course of the reaction. The products with the least amount of strain were obtained, namely 3,5-dehydrodiamantane (17) and pentacyclo[8.3.1.02,8.04,13.07,12]tetradec-5-ene (19, protodiamantene). The ease of separation of the cyclopropanic and olefinic products makes these reactions synthetically useful." @default.
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• W2111632015 date "1977-01-01" @default.
• W2111632015 modified "2023-09-28" @default.
• W2111632015 title "The mechanism of pyrolysis of polycycloalkyl sulfonates" @default.
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• W2111632015 doi "https://doi.org/10.1016/0040-4020(77)80148-8" @default.
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