Topics in current chemistry, 088, Organic Chemistry, by L. Birkofer

By L. Birkofer

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By L. Birkofer

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Other reports 67' 68, 69) confirm the highly stereospecific course of reaction (e. g. 67 ~ 78, 63 ~ 80) during the electrophilic displacement. However, it must be noted that the use of hydrobromic acid with 1,1-bis(trimethylsilyl)ethene (67) leads to 1-TMS-ethene (79). Sulfonation is applicable, too 7~ If the sulfonation reagent C1-SO2-O-TMS is added to 1-triethylsilylethene (61a) the corresponding sulfonyl compound (81) can be prepared, but an exchange of TES against TMS is observed (Scheme 9).

Propiophenone (184) gives by treatment with ethyl TMS acetate (185)[tetrakis(n-butyl)amine fluoride 1-trimethylsiloxy-2methyl-styrene (186) t 30) Cyclohexanone reacts with the combination dimethylTMS-amine (18 7)/p-toluenesulfonic acid to 1-trimethylsiloxy- 1-cyclohexene (188) a31). Similarly, acetylacetone plus phenyl-triethylsilyl-sulfide (189) afford 2-triethylsiloxy2-pentene-4-one (190) 132). 51 L. Birkoferand O. Stuhl CF~--~-0TMS C%o I /C=O C~ ~2C--OTMS CH3 C co~-c-c"~-c"3 0 ! _88} CHa-C - - C~H ~ - ~- C - - ~I C H ~ ~~ 0 0 TES-S~ (189| ~,~ CH~--C=CH--C--CH 3 ~ ~ J~ OTES 0 cmoj Scheme 28 Because of their good reactivity and the good access, silyl enol ethers are important intermediates for a variety of products as shown below (Scheme 28).

V. : J. Am. Chem. Soc. 95, 8005 (1973); b. Schleyer, P. v. , Williams, J. , Blanchard, K. : J. Am. Chem. Soc. 92, 2377 (1970) 40. : J. Am. Chem. Soc. 96, 2168 (1974) 41. , Beckhaus, H. : Chem. Ber. 1979 in print 42. : J. Chem. Phys. 44, 4283 (1966) 43. Beckhaus, H. : Chem. Ber. 110, 878 (1977) 44. : unpublished 45. Riichardt, C. et aL: Angew. Chem. 89, 913 (1977); Angew. Chem. Int. Ed. Engl. 16, 875 (1977) 46. : J. Chem. Phys. 43, 352 (1965) 47. Baxter, S. G. : J. Am. Chem. Soe. submitted 48. Beekhaus, H.

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