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The synthesis of 6,6,6-2H3-2E-hexenal

✍ Scribed by Simon Fielder; Daryl D. Rowan

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
285 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

6,6,6‐^2^H~3~‐2E‐Hexenal, leaf‐aldehyde, has been synthesized in 45% yield and 99.3% purity by reaction of 3,3,3‐^2^H~3~‐n‐propyl magnesium bromide with an ethereal solution of 3‐trimethylsiloxy‐2‐propenal (3) prepared in situ. This new one pot procedure alleviates the need to isolate (3) and should prove useful in the synthesis of other E‐α,β‐unsaturated aldehydes.

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The synthesis of 3,4-2H2-3Z-hexenal and
The synthesis of 3,4-2H2-3Z-hexenal and 6,6,6-2H3-3Z-hexenal
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with the DessNartin periodinane (1) in fluorotrichloromethane (freon 11). Use of the freon solvent greatly improved the recovery of this volatile aldehyde. Similarly the oxidation of 3,4-2Hz-3Z-hexen-1-ol (5) yielded 3,4-'HZ- 3Z-hexenal (6) in a 92% isolated yield with a purity of greater than 99%.

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## 2 , : 'H-NMR (CDCI,): 5.93 (dd, J = 10.7. 1.5); 5.67 6a. 7.7,8,octun-S-oiir @a): 'H-NMR (CDCI,): 3.98, 3.78 ( A R , . 0 ] o l l a l r (9a): ' H-N MR (CDCI,) : 4.02, 3.65 (.4 R, -c/io.~-aspiro~3.5/nori-X-i~.nr~ (7b): 'H-NMR (CDCI,): 6.04 (d, J = 10.4); 5.63 (d, ( d , J = 10.7);4.I0(dd,J=11.7,1.