OKSDATH-MANSILLA GABRIELA
Congresos y reuniones científicas
Título:
? Nucleofilic Substitution Reaction of 2-Aryl-1,3-.Dithiane Anions with Neopentyl and Neophyl Iodides.
Autor/es:
OKSDATH MANSILLA, GABRIELA; PEÑÉÑORY, ALICIA B.
Lugar:
Los Cocos, Córdoba, Argentina
Reunión:
Congreso; ?9th Latin American Conference on Physical Organic Chemistry? (CLAFQO 9); 2007
Institución organizadora:
CLAFQO
Resumen:

NUCLEOPHILIC SUBSTITUTION REACTIONS OF NEOPENTYL AND NEOPHYL

IODIDES WITH 2-ARYL-1,3-DITHIANE ANIONS

Gabriela Oksdath Mansilla and Alicia B. Peñéñory

Instituto de Investigaciones en Físico Química de Córdoba (INFIQC), Depto Química Orgánica, Fac.

de Ciencias Químicas, UNC, Córdoba (5000), Argentina.

E-mail: penenory@fcq.unc.edu.ar

penenory@fcq.unc.edu.ar

1,3-Dithiane anions are often used as acyl anion equivalents for C-C bond forming

reactions,1 which is a common and successful strategy for the construction of complex natural

products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

products.2 These anions react with common electrophiles such as alkyl, allyl and benzyl halides,

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

aldehydes, ketones and carboxylic acid derivatives by polar mechanisms. Furthermore, the

participation of 2-lithio-1,3-dithiane as electron donor was suggested in the reaction with a

neopentyl-type radical probe 5,5-dimethyl-6-iodo-1-hexene, with formation of 6-11% of cyclized

alkylated product.3 These reactions were performed at very low temperature (-20°C) in THF or THFTMDA

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the reactions of 2-aryl-1,3-dithiane anions (1) with

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

neopentyl (2a) and neophyl (2b) iodides under a variety of conditions in DMSO at 20°C. Thus, 1

as solvent, and a chain process was disregarded.

To further explore the possibility of dithiane anions as electron donors in a radical

nucleophilic substitution (SRN1),4 we have studied the r