Two new partially saturated tricyclic ring systems, 6, 6a,
7
,
8
,
9
, 10, 10a, 11-octahydro-11-oxodibenz [
b
,
e
] oxepins (3a and 3
b
), and -thiepins (
4
a and
4
b
) were synthesized. Compounds
4
a and
4
b
were desulfurized to give a pair of isomeric 2-methylbenzoylcyclohexanes (10a and 10
b
). Deuterated
4
a and
4
b
(11a and 11
b
) were prepared starting from butadiene-d
6 (12). The stereochemical features of 3a (trans), 3
b
(cis),
4
a (trans) and
4
b
(cis) are compared with those of 10a, 10
b
, 11a and 11
b
on the basis of proton nuclear magnetic resonance data.
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