ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES
The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external...
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| Published in | Journal of organic chemistry Vol. 60; no. 2; pp. 345 - 352 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
Amer Chemical Soc
27.01.1995
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| Subjects | |
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| Abstract | The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored. |
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| AbstractList | The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored. |
| Author | CURRAN, DP BALOG, A GEIB, SJ |
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| References | HUDLICKY, M (WOS:A1993MJ61000002) 1993; 58 WU, YJ (WOS:A1988Q440700004) 1988; 29 BURNELL, DJ (WOS:A1990DN45700002) 1990; 68 BALOG, A (WOS:A1995QE61900011) 1995; 60 WU, YJ (WOS:A1993MC95700006) 1993; 71 JOHNSON WS (WOS:A1995QE61900012.8) 1972; 94 OVERMAN, LE (WOS:A1988L843800058) 1988; 110 PANDEY, B (WOS:A1989AR55500015) 1989; 19 MASSEY AG (WOS:A1995QE61900012.11) 1967; 10 OVERMAN, LE (WOS:A1992KG62000018) 1992 GEMAL, AL (WOS:A1980KC87300021) 1980; 21 DEV S (WOS:A1995QE61900012.3) 1981; 37 HARDING, CE (WOS:A1992HB87500019) 1992; 57 MCCANN, SF (WOS:A1987K315400033) 1987; 109 WHITE, EH (WOS:A1968B604000044) 1968; 90 SONOGASHIRA, K (WOS:A1975AY12700010) 1975 MELLOR, M (WOS:A1978FG17000007) 1978 SHIMADA, J (WOS:A1984SJ28800035) 1984; 106 JOHNSON WS (WOS:A1995QE61900012.9) 1988; 110 WU YJ (WOS:A1995QE61900012.21) 1994; 59 HARDING, CE (WOS:A1989AC85000018) 1989; 54 LANSBURY, PT (WOS:A1975V342900030) 1975; 97 |
| References_xml | – start-page: 4467 year: 1975 ident: WOS:A1975AY12700010 article-title: CONVENIENT SYNTHESIS OF ACETYLENES - CATALYTIC SUBSTITUTIONS OF ACETYLENIC HYDROGEN WITH BROMOALKENES, IODOARENES, AND BROMOPYRIDINES publication-title: TETRAHEDRON LETTERS contributor: fullname: SONOGASHIRA, K – start-page: 528 year: 1978 ident: WOS:A1978FG17000007 article-title: SOME EPOXY-ACETYLENE CYCLIZATIONS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: MELLOR, M – volume: 106 start-page: 1759 year: 1984 ident: WOS:A1984SJ28800035 article-title: RING EXPANSION AND CLEAVAGE OF SUCCINOIN DERIVATIVES - GEMINAL ACYLATION, REDUCTIVE SUCCINOYLATION, AND STEREOSELECTIVE SPIRO ANNELATION METHODS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: SHIMADA, J – volume: 57 start-page: 883 year: 1992 ident: WOS:A1992HB87500019 article-title: MECHANISM OF THE INTRAMOLECULAR CYCLIZATION OF ACETYLENIC KETONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: HARDING, CE – volume: 29 start-page: 4369 year: 1988 ident: WOS:A1988Q440700004 article-title: A NEW ROUTE TO THE ZIZAANE SESQUITERPENES - AN EFFICIENT SYNTHESIS OF (+/-)-ISOKHUSIMONE publication-title: TETRAHEDRON LETTERS contributor: fullname: WU, YJ – volume: 110 start-page: 612 year: 1988 ident: WOS:A1988L843800058 article-title: NUCLEOPHILE-PROMOTED ELECTROPHILIC CYCLIZATION REACTIONS OF ALKYNES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: OVERMAN, LE – volume: 97 start-page: 394 year: 1975 ident: WOS:A1975V342900030 article-title: MODEL STUDIES FOR STEROID C-D RING SYNTHESIS - STEREOSELECTIVE HYDRINDAN FORMATION BY MEANS OF ACETYLENE-CATION CYCLIZATION publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LANSBURY, PT – volume: 54 start-page: 3054 year: 1989 ident: WOS:A1989AC85000018 article-title: MECHANISM OF THE TRANS-ANNULAR CYCLIZATION OF 5-CYCLODECYNONE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: HARDING, CE – volume: 60 start-page: 337 year: 1995 ident: WOS:A1995QE61900011 article-title: RING-ENLARGING ANNULATIONS - A ONE-STEP CONVERSION OF CYCLIC SILYL ACYLOINS AND OMEGA-ALKYNYL ACETALS TO POLYCYCLIC ENEDIONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: BALOG, A – volume: 58 start-page: 2229 year: 1993 ident: WOS:A1993MJ61000002 article-title: THE WICHTERLE REACTION publication-title: COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS contributor: fullname: HUDLICKY, M – volume: 21 start-page: 3195 year: 1980 ident: WOS:A1980KC87300021 article-title: HALOKETONE DEHALOGENATION BY IODIDE-ION publication-title: TETRAHEDRON LETTERS contributor: fullname: GEMAL, AL – volume: 109 start-page: 6107 year: 1987 ident: WOS:A1987K315400033 article-title: MEDIUM EFFECTS AND THE NATURE OF THE RATE-DETERMINING STEP IN MANNICH-TYPE CYCLIZATIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MCCANN, SF – volume: 68 start-page: 804 year: 1990 ident: WOS:A1990DN45700002 article-title: A SPIRO-ANNULATION APPROACH TO THE ZIZAANE SESQUITERPENES publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: BURNELL, DJ – volume: 90 start-page: 4734 year: 1968 ident: WOS:A1968B604000044 article-title: INTERCEPTION OF CARBONIUM IONS IN DEAMINATION OF 1-NORBORNYLAMINE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: WHITE, EH – volume: 94 start-page: 3013 year: 1972 ident: WOS:A1995QE61900012.8 publication-title: J AM CHEM SOC contributor: fullname: JOHNSON WS – volume: 110 start-page: 88 year: 1988 ident: WOS:A1995QE61900012.9 publication-title: J AM CHEM SOC contributor: fullname: JOHNSON WS – volume: 59 start-page: 1485 year: 1994 ident: WOS:A1995QE61900012.21 publication-title: CAN J CHEM contributor: fullname: WU YJ – volume: 19 start-page: 2741 year: 1989 ident: WOS:A1989AR55500015 article-title: A CONVENIENT SYNTHESIS OF SPIRO[4.N] DIONE AND 2,2-DISUBSTITUTED CYCLOPENTANE-1,3-DIONE SYSTEM publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: PANDEY, B – start-page: 995 year: 1992 ident: WOS:A1992KG62000018 article-title: PREPARATION OF UNSATURATED 7 AND 8 MEMBERED NITROGEN-HETEROCYCLES BY IODIDE-PROMOTED ALKYNE-IMINIUM ION CYCLIZATIONS publication-title: SYNLETT contributor: fullname: OVERMAN, LE – volume: 37 start-page: 1577 year: 1981 ident: WOS:A1995QE61900012.3 publication-title: TETRAHEDRON contributor: fullname: DEV S – volume: 10 start-page: 1 year: 1967 ident: WOS:A1995QE61900012.11 publication-title: ADV INORG CHEM RAD contributor: fullname: MASSEY AG – volume: 71 start-page: 1311 year: 1993 ident: WOS:A1993MC95700006 article-title: FORMATION OF 2,2-DISUBSTITUTED 1,3-CYCLOPENTANEDIONES FROM KETALS WITH 1,2-BIS(TRIMETHYLSILYLOXY)CYCLOBUTENE publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: WU, YJ |
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| Title | ADDITIVE AND MEDIUM EFFECTS ON LEWIS ACID-PROMOTED CATIONIC PI-CYCLIZATIONS OF ALKENYLCYCLOPENTANE-1,3-DIONES AND ALKYNYLCYCLOPENTANE-1,3-DIONES |
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