1973
DOI: 10.1021/ja00799a057
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Chemistry of bent bonds. XLII. Stereospecific rearrangement of strained cyclobutylcarbinyl cations

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Cited by 12 publications
(3 citation statements)
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“…48 Other approaches toward the bicyclo[4.3.1]decene skeleton are depicted in Scheme 7. These include Wells' pyrolysis of a secondary benzoate (36 f 37), 55 a rearrangement discovered by Gassman in his solvolysis studies of bridgehead cyclopropane derivatives (38 f 39 and 40 f 39), 56,57 House's β-elimination of a tertiary bromide and an alkoxide (41 f 42 and 43 f 42), 58 and Bestmann's intramolecular Wittig olefination (44 f 42). 59 Some of these methods are quite high yielding and have paved the way for synthetic efforts directed at the phomoidrides (see below).…”
Section: Synthetic Studiesmentioning
confidence: 99%
“…48 Other approaches toward the bicyclo[4.3.1]decene skeleton are depicted in Scheme 7. These include Wells' pyrolysis of a secondary benzoate (36 f 37), 55 a rearrangement discovered by Gassman in his solvolysis studies of bridgehead cyclopropane derivatives (38 f 39 and 40 f 39), 56,57 House's β-elimination of a tertiary bromide and an alkoxide (41 f 42 and 43 f 42), 58 and Bestmann's intramolecular Wittig olefination (44 f 42). 59 Some of these methods are quite high yielding and have paved the way for synthetic efforts directed at the phomoidrides (see below).…”
Section: Synthetic Studiesmentioning
confidence: 99%
“…4,17 Although relatively less strained when compared to the cyclopropyl group, the cyclobutyl ring, in the puckered conformation, is stereoelectronically well positioned for the formation of nonclassical cyclobutylmethyl cations. 18,19 There is much precedence for the involvement of nonclassical cyclobutylmethyl cations as reaction intermediates based on early solvolytic studies on cyclobutylmethyl substrates. [19][20][21][22][23][24][25][26][27][28][29][30] We have recently prepared the first persistent cyclobutylmethyl cation, R,R-dicyclopropylcyclobutylmethyl cation, 4, in superacid media.…”
Section: Introductionmentioning
confidence: 99%
“…18,19 There is much precedence for the involvement of nonclassical cyclobutylmethyl cations as reaction intermediates based on early solvolytic studies on cyclobutylmethyl substrates. [19][20][21][22][23][24][25][26][27][28][29][30] We have recently prepared the first persistent cyclobutylmethyl cation, R,R-dicyclopropylcyclobutylmethyl cation, 4, in superacid media. 31 The latter carbocation shows distinct absorptions (δ 13 C) for the cyclopropyl C R and C R′ as well as C β and C β′ carbons indicating that it exists as a bisected conformer.…”
Section: Introductionmentioning
confidence: 99%