By L. Birkofer
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The 1st NATO technology discussion board used to be held in Biarritz in September 1990. This Taormina convention is the second one in a chain that we want to be an extended one and that i think that it has equalled the good fortune of its predecessor. In developing those conferences the NATO technological know-how Committee desired to assemble top specialists to study fields of sturdy current curiosity.
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Extra info for Topics in current chemistry, 088, Organic Chemistry, Synthesis and Reactivity, 1980-03
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).
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