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The usual oxidative rearrangement then provides allylic alcohols (Scheme 51),140 2 V OAc SiMe, S e P h OAc iii -P OAc OH Reagents: i, PhSeCl; ii, SnCI, or Florisil; iii, H20,-py Scheme 51 Internal acetylenes react with isobutylmagnesium halides in ether in the presence of a catalytic amount of Cp,TiC12 to affordE- alkenyl Grignard reagents in almost quantitative yields. The regioselectivity of this hydromagnesiation is high for alkylarylacetylenes (Scheme 52) and silylacetylenes, but is less satisfactory for unsymmetrical dialkylacetylenes.

Ng and H. Alper, J. Org. , 1981,46, 1039. K. Takai, I. Mori, K. Oshima. and H. , 1981, 22,3985. Y. Tamaru, M. Kagotani, R. Suzuki. and Z. Yoshida, J. Org. , 1981,46,3374. 38 General and Synthetic Methods p-Lactams”* and t - a m i d e ~ havebeen ’~~ used for the first time as the carbonyl components in Wittig reactions. In addition, intramolecular Wittig reactions between phosphorane and carbonate functionalities have been used for the first time; the products are 2-phenoxychromones, for example (133), whose derivatives have recently emerged as a new class of natural p r o d u ~ t .

L4 (85) (86) X = C1, Br, or I Reagents: i, MeS02CI-K2C0,; ii, PhCH2NEt3X-BF, n ? g. 'I2 'I3 'I4 J. P. Marino and R. J. Linderman, J. Org. , 1981,46, 3696. C. J. Kowalski and K. W. Fields, J. Org. , 1981,46, 197. C. Shih and J. S. , 1981, 22,4217. g. 12' Reagents: i, 3NaH or 3NaOEt; ii, R'CHBrC0,H; iii, R2CHO; iv, H 2 0 Scheme 44 HO. A x o % R CO,H (X= H or CH20H) Reagents: i, H2NCMe2CH20H;ii, HCHO-KOH; iii, H' Scheme 45 '16 'I7 120 G. A. Russell, B. Mudryk, and M. Jawdosiuk, Synthesis, 1981,62.

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A review of the literature published during 1981 by Frank Northen Magill


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