Aromatic Alkylation. I. Intact Alkylation of Benzene and Toluene with Diisobutene

Sanford, Robert A.; Kovach, Stephen M.; Friedman, Bernard

doi:10.1021/ja01120a527

Cited by 5 publications

(4 citation statements)

References 3 publications

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“…As previously pointed out (27), solutions of aluminum chloride in nitromethane yielded intact alkylates at 25°C . ; the complex seemed less prone to cleave ieri-octylated products than aluminum chloride itself (Figure 4).…”

Section: Belowmentioning

confidence: 52%

See 1 more Smart Citation

Intact Alkylation of Benzene - Some Unusual Differences in Catalyst Systems

Sanford¹,

Kovach²,

Friedman³

1959

Ind. Eng. Chem.

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Section: Belowmentioning

confidence: 52%

“…In only three instances was intact alkylation accomplished (10,27,28). Later, it was reported (19) that by proper choice of catalyst and conditions, either depolyalkylation or intact alkylation could be made to predominate, but no data were given regarding intact alkylation with diisobutene.…”

mentioning

confidence: 99%

Intact Alkylation of Benzene - Some Unusual Differences in Catalyst Systems

Sanford¹,

Kovach²,

Friedman³

1959

Ind. Eng. Chem.

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“…These groups noted that tert-butylbenzene was a product in electrophilic aromatic substitutions using either diisobutylene or triisobutylene as the alkylating agent [17,18].…”

Section: Polyisobutyl Derivatives Of Unactivated Arenesmentioning

confidence: 99%

Synthesis of aryl-substituted polyisobutylenes as precursors for ligands for greener, phase-selectively soluble catalysts

Bergbreiter

Hobbs

Tian

et al. 2009

Pure and Applied Chemistry

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General synthetic approaches to functional derivatives of polyisobutylene (PIB) that contain arene groups that can be used as catalysts or as precursors to catalyst ligands are discussed. The emphasis is on reactions that use commercially available terminally functionalized PIB derivatives as starting materials. Both successful and unsuccessful electrophilic aromatic substitution processes are described, and potential problems of this process and ways to circumvent the problem of depolymerization of the intermediate polyisobutyl cation in substitutions of less reactive arenes are detailed. Examples that lead to polyisobutyl-containing arenes that are known and potentially useful as ligands or ligand precursors for greener homogeneous catalysts that are phase-selectively soluble and recoverable in heptane are emphasized.Scheme 2 Synthesis of a tertiary alcohol-terminated PIB that does not terminate in a diisobutylene group. The overall yield of 15 in this sequence varied between 28-34 %.

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“…RING-CLOSURE ALKYLATION fComplex) (Continued,) Product and Reagent Reference ).razulene, AlCl:i. (Z5L:) 4-Cl-benzanthrone, H2SO.1 (also for 9-and 10-) (19V) Naphtho [2,3-e jpyrene, A1C1«, NaCl (SV) 4,5,ó,…”

Section: Open-chain Alkylation (Aromatics)mentioning

confidence: 99%