Nonplanar Cyclobutane. I. The 3-Isopropylcyclobutyl System. Nuclear Magnetic Resonance Spectra of Alcohols and Amines

Lillien, Irving; Doughty, R. A.

doi:10.1021/ja00977a035

Cited by 25 publications

(2 citation statements)

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“…During the past several years, a good deal of physical information has accumulated which supports a nonplanar structure for cyclobutane. [25][26][27][28][29][30][31][32] The nonplanar conformations lead to axial and equatorial positions similar to those of cyclohexane and are indicated in Chart I. The cyclobutyl ring is quite flexible and…”

Section: Mechanistic Results and Discussionmentioning

confidence: 99%

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Photochemical transformations of small ring carbonyl compounds. XIX. Photochemistry of benzoylcyclobutanes

Padwa¹,

Alexander²,

Niemcyzk³

1969

J. Am. Chem. Soc.

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The photolysis in benzene of cyclobutyl phenyl ketone has been found to afford four products. The structures have been assigned as l-phenyl-4-penten-l-one, 2-hydroxy-2-phenylbicyclo[l.l.l]pentane, cyclobutylphenylcarbinol, and the pinacol of starting material. The formation of the keto olefin and the bicyclopentanol is considered to proceed through a diradical intermediate formed by transannular hydrogen abstraction by the excited -* triplet. The inefficiency of the photoreaction, both in terms of quantum yield and rate, is attributed to the unfavorable geometry required for internal hydrogen transfer, cis-and zron.s-2-phenylcyclobutyl phenyl ketones undergo rapid photointerconversion followed by a further intramolecular reaction to produce l,5-diphenyl-4penten-l-one. The photoisomerization has been rationalized by homolytic ring cleavage of the cyclobutyl ring.

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Section: Mechanistic Results and Discussionmentioning

confidence: 99%

“…Steady-state radical concentrations and decay constants were obtained by methods that have previously been described. 31 The photochemical behavior of three-ring carbonyl compounds has been the subject of extensive study.6 Although much remains to be learned about (1) For part XVIII, see A. Padwa and R. Gruber, J. Am.…”

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confidence: 99%

Photochemical transformations of small ring carbonyl compounds. XIX. Photochemistry of benzoylcyclobutanes

Padwa¹,

Alexander²,

Niemcyzk³

1969

J. Am. Chem. Soc.

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Reduction of 3-Substituted 1-Arylcyclobutanols

Kinnius

Dehmlow²

2000

J. prakt. Chem.

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421In the context of our work on novel model compounds for liquid crystals which contain cyclobutyl groups, [1 -4] we were interested in an effective benzylic alcohol →hydrocar-bon conversion of 1-arylcyclobutanols 1 to give compounds 2. Ideally this should be a one-pot process.Hydrogenolysis as well as elimination/catalytic hydrogenation led to unpleasant product mixtures frequently. Likewise, Olah's method (Pd/cyclohexene/AlCl 3 ) [4] or our own previous procedure (Me 2 NBH 2 /TiCl 4 ) [5] gave unsatisfactory yields oftentimes. When, however, compound 1a was treated with lithium aluminumhydride/aluminum trichloride in tert-butyl methyl ether according to Brewster et al. [6], 2a was obtained in 51% as a 58:42 mixture of trans and cis isomers. Both chemical yield (93%) and stereoselectivity (7:3) where improved when applying a modification of the method of Gribble et al. (NaBH 4 in CF 3 COOH) [7,8].Consequently, this last mentioned procedure was applied to an entire series of 3-substituted 1-arylcyclobutanols 1a -1o. A preponderance of the desired trans isomers (52 -76%) was observed in all cases, and most chemical yields were satisfactory (Table 1) Abstract. A useful and specific method for the the title reaction (1 → 2) involves treatment with NaBH 4 in CF 3 COOH whereas other procedures from the literature yield hard-toseparate mixtures.

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Stereochemistry of Cyclobutane and Heterocyclic Analogs

Moriarty

1974

Topics in Stereochemistry

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Nonplanar Cyclobutane. I. The 3-Isopropylcyclobutyl System. Nuclear Magnetic Resonance Spectra of Alcohols and Amines

Cited by 25 publications

References 1 publication

Photochemical transformations of small ring carbonyl compounds. XIX. Photochemistry of benzoylcyclobutanes

Photochemical transformations of small ring carbonyl compounds. XIX. Photochemistry of benzoylcyclobutanes

Reduction of 3-Substituted 1-Arylcyclobutanols

Stereochemistry of Cyclobutane and Heterocyclic Analogs

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