Preparation of 2-substituted 2-cyclohexen-1-ones

Tobias, M. A.; Strong, Jerry G.; Napier, Roger P.

doi:10.1021/jo00830a113

Cited by 38 publications

(5 citation statements)

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“…The synthesis of chromophores 1 − 3 is depicted in Scheme . In the presence of sodium ethoxide as the base, 1-butanethiol can be easily deprotonated to form a nucleophilic thiolate which underwent ring-opening reaction of epoxyisophorone 4 to selectively generate 2-SBu-substituted isophorone 5 in a nearly quantitative yield . This intermediate can be reacted directly with 4-diethylaminobenzaldehyde 7 in one-pot via the Knoevenagel condensation to furnish aminophenyldienone 9a with a high overall yield of 75%.…”

Section: Resultsmentioning

confidence: 99%

Donor−Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

et al. 2008

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We have successfully utilized epoxyisophorone ring-opening chemistry to efficiently incorporate the butylthio group to the phenyltetraene bridge of highly efficient nonlinear optical chromophores in high overall yield. By following the guidance of Dewar’s rules, the sulfur atom functions as a moderate π-accepting group at a starred position of the conjugated bridge. Several of very critical material parameters of the phenyltetraenic chromophores for device applications have been intrinsically and simultaneously improved through such a simple and straightforward engineering of molecular structures. Compared with the nonsubstituted analogue 2, thiolated chromophore 1 achieves higher molecular hyperpolarizability (34%), enhanced E-O coefficient (38%), significantly improved photochemical stability against 1O2 (by an order of magnitude), and better optical transparency (17 nm blue-shifted λmax absorption spectrum).

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Section: Resultsmentioning

confidence: 99%

Donor−Acceptor Thiolated Polyenic Chromophores Exhibiting Large Optical Nonlinearity and Excellent Photostability

et al. 2008

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“…17 Since then, no modifications of this procedure were proposed. Noteworthy only are the studies, 139,140 which were not included in the cited review, and the investigations 141,142 reported at a later time.…”

Section: B Oxirane-ring Openingmentioning

confidence: 99%

Captodative aminoalkenes

Rulev¹

2002

Russ. Chem. Rev.

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“…76-82 "C/0.4 mmHg, RF(B) 0.35; spectroscopic data were identical to those of a sample prepared24 by rearrangement of (17). (15).-Butyl-lithium (1.5~ solution in hexane; 1.3 ml, 2 mmol) was slowly added to a stirred, cooled ( -10 "C) solution of bisphenylthioethane (0.42 g, 2 mmol) in dry THF (10 ml) under a nitrogen atmosphere. After 15 min the anion was quenched with phenylacetaldehyde in dry THF (50% w/v) until the yellow colour was just discharged.…”

Section: -Phenylthiopent-3-en-2-one (1 B)mentioning

confidence: 99%