[amcavoy]

When reacting 1,2,2,6-tetramethylcyclohexanol with POCl3 and pyridine, why doesn't the product follow Zaitsev's Rule?  My professor said that a double bond would form between the 1-carbon and the 1-methyl carbon rather than the 1-carbon and the 6-carbon (as I would expect).  Why is this so?  Also, what is the name of this product?

Thanks.

[sjb]

Was it a particular diastereomer that you were told would not form the alkene between carbons 1 and 6?

The only thing I can think of at the moment is that the OH and the methy group at C₆ were trans to each other, so antiperiplanar elimination may not occur.

Which compound did you want to know how to name - your expected or the observed?