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Acetolysis of 1,3-di-t-butylpropargyl tosylate

✍ Scribed by Roger S. Macomber

Book ID
104222586
Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
247 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis

A comma example of allylic-type interaction, often encountered at the undergraduate level, is the resonance between propargyl end allenic structures (e.g. Scheme 1, z-m).

A search ol" the literature reveals, however, that relatively little recent work hes been done ou the fcmation and reactions of substituted propszgyl (@ sXlenic) cations. Burawoy snd Spinner investigated (' the solvolysis of a series of tertiary halides RC=C-C(CIi&-X in 8@ aqueous ethancl, and found that the triple bond "efficiently transmitted polar effects," as inferred from relative solvolytic rates. The pyoducts from these reactions were not identified. Wre recently the pm spectraof severaltertiarypropargylcarb~~ions iu "super acid" have been obtsin&2J'

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Brown and Chloupek (1) have reported that the introduction of a-methyl groups in s series of 1-chloro-1-methylcyclopentsnes csuses an increase in the ethsnolysis rate (e.g., l-chloro-1,2,2,5,%pentsmethylcyclopentsne reacts 82 times faster than 1-chloro-1-methylcyclopentsne). The increased solvolysia