By Royal Society of Chemistry, W. Parker, Parker W

ISBN-10: 0851865828

ISBN-13: 9780851865829

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Example text

281 CN C1 (222) i (223a) (223b) KOBu‘ CN CN Photochemical addition of allene to the enal(228) results in formation of a product (229; R = CHO), whose stereochemistry was established by conversion into the mesylate (229; R = CH20Ms)and solvolytic rearrangement of the latter to (230; R = H and Ms). e. 282 ’” J. Kiji, S. Yoshikawa, E. Sasakawa, S. Nishimura, and J. Furukawa, J. , 1974,80,267. 280 281 ’’’ S . Farber and R. T. , 1974,4, 243. H. K. Hall, jun. and R. E. Yancy. J. Org. , 1974,39,2862. F.

X X Thermally254 and photochemically25 5 induced cross-condensations of two dissimilar olefins have also been reported. 2s7All the evidence to date is consistent with a mechanism involving an intermediate 1,4-dipole. Thus, whereas the enol ether (200) reacts with TCNE in aprotic media to give the cyclobutane (201) quantitatively, in methanol the intermediate zwitterion is trapped, affording 70% of (202) and 30% of (201). It was shown that (201) does in fact ring-open to (202) in methanol, but at a much slower rate than that at which (202) is formed from (200) and TCNE.

A. Paquette, J. Arner. Chem. ,1974, 96,4715. T. Tezuka, 0. Seshimoto, and T. S. Chem. , ,1974, 373. F. Mathey and J. P. Lampin, Fr. P. 2 171 596. ,197481,25805). D. 1. Schuster and C. W. Kim, J. Amer. Chem. , 1974,96, 7437. K. Shudo and T. Okamoto, Chem. and Pharm. Bull. (Japan),1974,22, 1204. C . R. Flynn and J. Michl, J. Amer. Chem. , 1974, 96, 3280. 62 Alicyclic Chemistry eph 0 hv o4 pr-H 'Ph r i 254nmt ' \ (273) >345nm \ (274) benzocyclobutene (276), with some of the cis-isomer also being formed by isomerization of (276) at still higher temperatures.

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Alicyclic Chemistry: Volume 4: A Review of Chemical Literature (Spr Alicyclic Chemistry (Rsc)) by Royal Society of Chemistry, W. Parker, Parker W


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