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Dewar, and Z. B. Maksic, J. Amer. Chem. ,1973,95,5245. N. D. Epiotis, J. Amer. Chem. ,1973,95,3807; R. Hoffmann, C. C. Levin, and R. A. , p. 629. 36 Alicyclic Chemistry ammonium salt) is one of the easiest and most reliable methods of generating dichlorocarbene for addition to olefins. '^ The use of this method has made possible the isolation of good yields of the di-adducts (195) as well as the mono-adducts (194) of dichlorocarbene with allenes (193; R', R2, R3,R4 = H, Me). With phenylallene (193; R' = Ph, R2 = R3 = R4 = H), elimination of HC1 from the di-adduct takes place with ring-opening, and further addition of dichloro-carbene to the acyclic double bond of the newly generated olefm (196) results in the formation of (197).
Nakadaira, Tetrahedron, 1973,29,275. Three- and Four-membered Rings 31 Ph (163) a ; R b; R Ph =H = Me (164) 10% 0% 0% 6% 9% 10% Ph A __t (165) I + EtCH=C-COMe (166) ( I 64b) Scheme 15 (167) X = CR, o r 0 (168) Some reactions of interests5 which also involve cyclopropane formation from a propene are shown in Scheme 16. so P hv RO R = Me E? RO or OAc Scheme 16 85 H. Nozaki and N. Miyamoto, Tetrahedron, 1973, 29, 3819; G. Pattenden and M. Bullivant, Pyrethrum Post, 1973,12, 64. 86 Sensitized photolysis of the parent allyl halides (169; X = C1 or Br) affords the cyclopropanes (170; X = Cl or Br) in 10% yield, whilst the butenyl chloride (171) gives the allylic isomer (172) and isomeric cyclopropanes (173) and (174).
Sondheimer, J. , 1973,38,2715. Klug, and A. Breuer, Org. , 1973,53, 164. R. A. Moss and F. G. Pilkiewicz, Synthesis, 1973,209. 41 Three- and Four-membered Rings \ MeOMe OMe c It Me0 c I1 OMe Me0 CHBr, __* (Ref. 11 1) KOBu' OMe R1 R' 'R -MeSCHCl, R ' (Ref. ' l 5 The initial adducts (216) from the 2-olefins (215) were debrominated in two steps by treatment with zinc and acetic acid followed by ethyl-lithium to give cyclopropanes (217). This sequence was equally successful and stereospecific when applied to the corresponding E-olefins.