Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry

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Extra info for Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry Volume 1 Part 1 a review of the literature published during 1970 and 1971

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T. Bottini, F. P. Corson, R. Fitzgerald, and K . A . Frost, Tetrahedron Letters, 1970, 4757. -Allylic halides undergo solvolysis at rates greater than those of their saturated analogues owing to charge delocalization through the mystem. The vinyl cation,152it may be anticipated, could be D & ButOIl, IOBut D@But MDBUt D D h (211) X = C1, Rr, or I D D Scheme 12 similarly stabilized by such a neighbouring double bond. This is demon~ t r a t e din l ~solvolyses ~ of the allenic chlorides (213), which proceed readily in c1 ‘X (213) X = H or OMe 15* lS3 M.

1971, 156. Ar I Ph (197) R Aliphatic, Alicyclic, and Saturated Heterocyclic Chemistry 44 The rearrangement is formulated as passing through a heterolytic cleavage of the N-0 bond, but a radical mechanism seems more likely. The cycloaddition of alkenylidenecyclopropanes (198) with the triazoline (199) involves participation of the strained o-bond of the cyclopropane. A concerted reaction is believed to be involved since single isomers of (ZOO) and (201) are obtained which are the least thermodynamically ~ t a b 1 e .

Simpson and D. W. Burt, Tetrahedron Letters, 1970, 4799; D. W. Burt and P. Simpson, J . Chem. ( C ) , 1971, 2872. R. Tanaka and S. I. Miller, Tetrahedron Letters, 1971, 1753. R . Tanaka, M. Rodgers, R. Simonaitis, and S. 1. Miller, Tetrahedron, 1971,27,2651. 89 J ,R Among Cope rearrangements involving acetylenes is the thermolysis of hex-5-en-l-yn-3-01. The products were all considered to be derived by further reaction of the primary oxy-Cope rearrangement product (118). u. g1 OB O0 91 M. E. Hendrick, W.

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