Tetra-n-butylammonium fluoride supported on glass helices was used to generate cyclopropenes in the gas phase from β-halocyclopropylsilanes using the vacuum gas-solid reaction (VGSR) technique. Bicyclo (4.1.0) hept-1,7-ene (1), bicyclo (4.1.0) hept-1,6-ene (2), and bicyclo (5.1.0) oct-1,8-ene (3) were prepared from the appropriate β-chlorocyclopropylsilanes.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) Compounds 1 and 2 underwent ene reactions to give the same dimer 4. Compound 4 isomerized to 5 via cyclopropene-vinyl carbene rearrangements. Dimerization of 4 led to the cycloaddition adducts 6 and 7 (tetramers of 1).(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) Treatment of either 4 or 5 with oxygen formed 2-(bicyclo (4.1.0) hept-1-yl)-1-cyclohexenecarboxaldehyde (8) and 1-(bicyclo (4.1.0) hept-1-yl)-cyclohepten-3-one (9).(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) Hydrogenation 4 and 5 below $-20\sp\circCyieldedproductsidentifiedprovisionallyas10and11,respectively.Both10and11rearrangedtomeso−1−(bicyclo(4.1.0)hept−1−yl)bicyclo(4.1.0)heptane(12).(DIAGRAM,TABLEORGRAPHICOMITTED...PLEASESEEDAI)Cyclopropene3alsoreactedviaanenereactiontogivebothdimerandtrimer.Tricyclo(5.5.0.0\sp{1,6}$) decane (13) was prepared by reduction of the butadiene Diels-Alder adduct of 3. Hydrogenation of 3 gave cis-bicyclo (5.1.0) octane and 1-methylcycloheptane.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)