Science of Synthesis

Tidwell, T. T., Science of Synthesis, (2006) 23, 588.

The thermolysis of ethyl ω-hydroxyalkynyl ethers ‌115‌ produces alkylketenes ‌116‌ by hydrogen transfer with elimination of ethene (‌Scheme 36‌).[‌94‌] The functionalized side chain bearing a pendant hydroxy group cyclizes intramolecularly to form the corresponding racemic lactones ‌117‌ (‌Scheme 36‌).[‌94‌] The addition of tributylamine (10 equiv) facilitates the cyclization reaction.

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Meeeeee Meeee ‌888‌	Meeeee ‌888‌	Meeeeee ‌888‌	Meeee (%)	Mee
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Meeeeeeeee ee (eeeeeeeeee)eeeeeeeeeee (‌888‌) ee eeeeeeee eeeee e eeeeeee ee eeeeeeeeeeee (88–88%) eee eeeeee eeeeeeeeeeeeeeeee (‌888‌, 88%).[‌88‌] Mee eeeeee eeeeeee eee ee eeeeee eeee eeeeeeeeeeeeeeee (‌888‌), eeeeeeee ee e eee eeeeeeeee ee eee eeeeeeeeee eeeee (‌Meeeee 88‌).

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References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.