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Tertiary Alchol Dehydration

Tertiary Alchol Dehydration - Organic Chemistry Forum

Tertiary Alchol Dehydration - Organic Chemistry Forum


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Old 12-09-2003, 04:45 PM
John Wilman
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Default Tertiary Alchol Dehydration



Are there any mechanisms/syntheses where a tertiary alcohol is
dehydrated in an non-carbocationic pathway? For instance, instead of
the "usual"

R CH3
| |
C - C - OH -> R = C (CH3)2
| |
R' CH3

I'm trying to get to

R
|
C - C = CH2
| |
R' CH3


A potential caveat is a double bond elsewhere in the molecule
that needs to be preserved. Additionally, R and R' form "opposite
ends" of a ring structure so stearic hindrance is also a problem.

I've looked at perhaps going to an alkyl halide then trying sn
SN2 to remove the halide, but haven't found a path for that either.

I've checked a few sources, including the orgsyn.com online
library, to no avail. Does anyone out there have any pointers or
suggestions I could check out? Thanks in advance.

John Wilman
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Paul J. Franklin(moderator - sci.chem.organic.synthesis)
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Georgia State University <[Only registered users see links. ].edu>
Atlanta, GA
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alchol , dehydration , tertiary


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