Alicyclic Chemistry Vol. 3 by W Parker;

By W Parker;

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Effenberger and W. Kurtz, Chem. , 1973, 106, 511. lo' lo' E. V. Dehmlow, H. -C. Hass, Annalen, 1973, 1063. J. Tsunetsugu, M. S. Chem. , 1973, 363. Alicyclic Chemistry 38 OMe OMe @ Me MeO& Me0 \ / OMe OMe It was initially reported that generation of dibromocarbene by the phasetransfer-catalysed method gave poor results. 'O3 were able to obtain reasonable yields (40-72 %) by employing longer reaction times (1-4 days), 1,2-divinylbenzene,for example, giving the adduct (205) in 50% yield. However, the di-adduct of tetramethylallene with dibromocarbene was obtained in only 10 % yield, compared with a 90% yield of the bis-dichlorocarbene adduct'" by the same method.

R. P. 376362 (Chem. , 1973,79, 52869). 22 Alicyclic Chemistry t-butyl alcohol and polar solvents such as DMF. This type of reaction has been reported previously. The benzothiepin derivatives (103; X = C1 or Br) cyclize in nearly quantitative yield62to the tricyclic compounds (104; X = C1 or Br). The influence of solvent and base strength on the cyclization was studied. A double intramolecular c y ~ l i z a t i o nhas ~ ~been used to synthesize the antitricyclohexane (106). Thus, the product (105) of photosensitized cycloaddition of trans-l,4-dichlorobut-2-ene to maleic anhydride, after conversion into the corresponding dimethyl ester, was treated with sodium hydride to furnish (106).

Gaudemare-Bardone and M. Gaudemar, Bull. chim. France, 1973,3467. Alicyclic Chemistry 52 IM C0,Et C0,Et / C0,Et C0,Et C0,Et (263) (259)+ RCHO - a; X b:X Br = H = - Br I C0,Et RCH-Cl I (362) C0,Et OMgBr (266) K ' = Me, Pr, or Ph Sodium hydride will effect hydrogen chloride elimination from the activated ally1 chlorides (267) and addition in toluene to electrophilic olefins (268) furnishes the vinylcyclopropanes (269a)and (269b)with the former predominating over the latter. 142 S. Ducher, J. P. Sudre, and R.

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