Nortricyclyl acetate

Bicyclo[2.2.1]hepta-2,5-diene, nitrosyl chloride adduct, 46, 74 reaction with acetic acid to yield nortricyclyl acetate, 46, 74 Bicyclohexyl, 46, 61 Bicyclohexylidene, 47, 34 ejSO-e s-BlCYCLO[3.3.0]OCTANE-2-CAR-BOXYLIC ACID, 47, 10 Bicyclopentadienylidene, octa-chloro-, 46,93... 

A. Nortricyclyl acetate. A mixture of 156 g. (1.70 moles) (rf bicyclo[2.2.l]hepta-2,5-diene (Note 1), 105 g. (100 ml., 1.75 moles) of glacial acetic acid, and 3 ml. of boron trifluoride ether- ate (Note 2) is placed in a 500-ml. flask attached to a condenser equipped with a drying tube. The mixture is heated on a steam bath for 6 hours, cooled to room temperature, and diluted with 250 ml. of ether. The ethereal solution is washed successively with two 50-ml. portions of 3A ammonia and 50 ml. of water and dried over magnesium sulfate. The ether is removed by distillation through a short column of glass helices, and the dark... 

H)-Naphthalenone, 4,4a,5,6,7,8-HEXAHYDRO-, 46, 80 Nitroacetone, 46, 3 />-Nitrobenzaldehyde, 46, 36 Nitrosation of N-phenylglycine, 46, 96 N-Nitroso-N-phenylglycine, 46, 96 reaction with acetic anhydride to yield 3-phenylsydnone, 46, 96 Nitrosyl chloride, addition to bicyclo [2.2.1]hepta-2,S-diene, 46, TS Nonane, 1,1,3-trichloro-, 46,104 Noriricvclanol, 46, 74 oxidation by chromic acid, 46, 78 NortricyclanOne, 46, 77 Nortricyclyl acetate, 46, 74 from bicyclo[2.2.1]hepta-2,5-dlene and acetic acid, 46, 74 saponification of, 46, 75... 

Quadricyclane is a highly strained and reactive compound. It reacts readily with acetic acid to give a mixture of nortricyclyl acetate and exo-norbornyl acetate and with bromine to yield a mixture of 2,6-dibromonortricyclene and exo-5-anti-l-dihvo-monorbornene.3 Quadricyclane undergoes cycloaddition reactions with a variety of dienophiles to give 1 1 adducts.15 1 2 3 4 5 6 7... 

Meinwald et al used nitrosyl chloride for convenient removal of the unwanted olefinic by-product (3) in the preparation of nortricyclyl acetate (2) by BFj-catalyzed... 

The products of the buffered acetolysis of 2-deuterio-eiido-norborn-5-en-2-yl p-bromobenzenesulphonate (91) have been analysed by mass spectrometric, C and H n.m.r. procedures, and the results discussed in a clearly written and interesting paper. The deuterium initially on C-2 had migrated partially on to C-1 (30%) in the deuteriated cxo-norborn-5-en-2-yl acetates so formed, and was equally and uniquely distributed between C-1 and C-6 of the deuteriated nortricyclyl acetate, the major solvolysis product. Within the limits of detection products derived from C( 1 -> 7) migration or from fragmentation were not formed. The results are consistent with the formation of the symmetrical nortricyclyl cation (92), or ion pair, from the norborn-5-en-2-yl cation, the isomerization being competitive with the reaction of these intermediates with solvent [n.b. C-1 and C-6 in (92) are equivalent positions that correspond to the C-1 and C-2 positions in the norbomenyl system]. 

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