Camphene, Wagner-Meerwein rearrangement with

Bomeol is oxidized to camphor with chromic or nitric acid dehydration with dilute acids yields camphene. Bomeol is readily esterified with acids, but on an industrial scale bornyl esters are prepared by other routes. For example, levorotatory bomeol is synthesized industrially from levorotatory pinenes by Wagner Meerwein rearrangement with dilute acid, followed by hydrolysis of the resulting esters [86]. 

Higher-chlorinated camphenes are the most plausible side products. They may be formed together with other cyclic carbon skeletons if the Wagner-Meerwein rearrangement (to polychlorinated bornanes) is hindered [38, 39]. The ionic addition of chlorine to the primary olefinic carbon is always in competition with radical chlorination. Although the first mechanism is more likely, the second one may also take place. It was found that a gentle chlorination of... 

A specialized cation rearrangement first observed with bornyl systems is the acid catalyzed rearrangement of camphene hydrochloride (73) to isobornyl chloride (76).32 The reaction, which proceeds by a 1,2-alkyl shift called the Wagner-Meerwein rearrangement, initially generates bornyl cation 74, but rearrangement to... 

Manganese(m) acetate oxidation (cf. Vol. 3, p. 34) of camphene gives (186) as a 95 5 mixture by carboxymethyl radical insertion no rearranged products were obtained, in contrast to /3-pinene which gave Wagner-Meerwein products only, and no free-radical insertion.279 The E- and Z-isomers of (187) probably result from a non-concerted biradical intermediate formed by benzyne addition to camphene.280 Benzyl-lithium adds to the aminocamphor (188) exclusively from the exo-side whereas only the competing enolization reaction occurs with more sterically hindered organometallics.281... 

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